Organic light-emitting device, and light-emitting material and compound used therefor

ABSTRACT

An organic light-emitting device having a light-emitting layer containing a compound represented by the general formula below has a high light emission efficiency. In the general formula, at least one of R 1  to R 5  represents a cyano group, at least one of R 1  to R 5  represents a 9-carbazolyl group, a 1,2,3,4-tetrahydro-9-carbazolyl group, a 1-indolyl group or a diarylamino group, and the balance of R 1  to R 5  represents a hydrogen atom or a substituent.

TECHNICAL FIELD

The present invention relates to an organic light-emitting device havinga high light emission efficiency. The invention also relates to alight-emitting material and a compound used therefor.

BACKGROUND ART

An organic light-emitting device, such as an organic electroluminescentdevice (organic EL device), has been actively studied for enhancing thelight emission efficiency thereof. In particular, various studies forenhancing the light-emitting efficiency have been made by newlydeveloping and combining an electron transporting material, a holetransporting material, a light-emitting material and the likeconstituting an organic electroluminescent device. There are studiesrelating to an organic electroluminescent device utilizing a compoundcontaining a carbazole structure and an indole structure, which arefound among them, and some proposals have been made hitherto.

For example, PTL 1 describes the use of as organic compound having acarbazole structure and an indole structure represented by the followinggeneral formula, as a host material of a light-emitting layer of anorganic light-emitting device. In the following general formula, m and neach represent an integer of from 1 to 5, provided that the sum of m andn is an integer of from 2 to 6; X represents an organic group having avalency of (m+n) which may have a substituent; and R₁ to R₁₄ represent ahydrogen atom, a halogen atom, an alkyl group, an aryl group or aheterocyclic group.

PTL 2 describes the use of a compound having two or more carbazolestructures, as a host material of a light-emitting layer of on organiclight-emitting device. PTL 3 describes the use of a compound having twoor more indole structures, as host material of a light-emitting layer ofan organic light-emitting device.

CITATION LIST Patent Literatures

PTL 1: JP-A-2005-174917

PTL 2: JP-A-2009-94486

PTL 3: JP-A-2009-76834

SUMMARY OF INVENTION Technical Problem

As described above, a compound containing a carbazole structure and/oran indole structure has been variously studied, and some proposalsrelating to application thereof to an organic electroluminescent devicehave been made. In most of the organic electroluminescent devices havingbeen proposed, however, the proposals therein are the use of a compoundcontaining a carbazole structure and/or an indole structure as a hostmaterial of a light-emitting layer. Furthermore, the light emissionefficiency thereof is not necessarily high. Moreover, it may not be saidthat all the compounds containing a carbazole structure and/or an indolestructure have been comprehensively studied. In particular, theusefulness of a compound containing a carbazole structure and/or anindole structure as a light-emitting material and the usefulness of acompound containing a carbazole structure or an indole structure andfurther containing plural cyano groups have almost not been studied.According to the studies having been made, a clear relationship has notyet been found between the chemical structure of the compound containinga carbazole structure and/or an indole structure and the usefulness ofthe compound as a light-emitting material, and it is the currentsituation that it is difficult to expect the usefulness as alight-emitting compound based on the chemical structure. The presentinvention have considered these problems and have made investigationsfor evaluating the usefulness of a cyanobenzene derivative having acarbazole structure, an indole structure and the like, as alight-emitting material of an organic light-emitting device. Theinventors also have made investigations for providing a general formulaof a compound that is useful as a light-emitting material, therebygeneralizing a constitution of an organic light-emitting device having ahigh light emission efficiency.

Solution to Problem

As a result of earnest investigations for achieving the objects, theinventors have clarified that a particular cyanobenzene derivativecontaining a carbazole structure, an indole structure and the like isextremely useful as a light-emitting material of an organicelectroluminescent device. In particular, the inventors, have found acompound that is useful as a delayed fluorescent material incyanobenzene derivatives containing a carbazole structure, an indolestructure and the like, and have clarified that an organiclight-emitting device having a high light emission efficiency may beprovided inexpensively. Based on the knowledge, the inventors haveprovided the following inventions as measures for solving the problems.

(1) A light-emitting material containing a compound represented by thefollowing general formula (1):

wherein, in the general formula (1), at least one of R¹ to R⁵ representsa cyano group, at least one of R¹ to R⁵ represents a group representedby the following general formula (11), and the balance of R¹ to R⁵represents, a hydrogen atom or a substituent;

wherein in the general formula (11), R²¹ to R²⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof the following requirements (A) and (B) is satisfied:

(A) R²⁵ and R²⁶ jointly form a single bond, and

(B) R²⁷ and R²⁸ jointly form an atomic group that is required forforming a substituted or unsubstituted benzene ring.

(2) The light-emitting material according to the item (1), which emitsdelayed fluorescent light.

(3) The light-emitting material according to the item (1) or (2),wherein at least one of R¹ to R⁵ represents a substituted orunsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4--tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted, or unsubstituted diarylamino group.

(4) The light-emitting material according to the item (1) or (2),wherein at least two of R¹ to R⁵ represent a substituted orunsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted, or unsubstituted diarylamino group.

(5) The light-emitting material according to the item (1) or (2),wherein at least one of R¹ to R⁵ represents a cyano group, and thebalance of R¹ to R⁵ each independently represents any of a hydroxygroup, a halogen atom, a substituted or unsubstituted 9-carbazolylgroup, a substituted or unsubstituted 1,2,3,4-9-carbazolyl group, asubstituted or unsubstituted 1-indolyl group or a substituted orunsubstituted diarylamino group.

(6) The light-emitting material according to the item (1) or (2),wherein at least one of R¹ to R⁵ represents a cyano group, and thebalance of R¹ to R⁵ each independently represents any of a substitutedor unsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group.

(7) The light-emitting material according to the item (1) or (2),wherein at least one of R¹ to R⁵ represents a cyan group, and thebalance of R¹ to R⁵ each represents a substituted or unsubstituted9-carbazolyl group.

(8) The light-emitting material according to the item (1) or (2),wherein at least one of R¹ to R⁵ represents a hydroxy group, at leastone of R¹ to R⁵ represents a cyano group, and the balance of R¹ to R⁵each represent a substituted or unsubstituted 9-carbazolyl group.

(9) The light-emitting material according to any one of the items (1) to(8), wherein at least one of R¹ to R⁵ represents a group represented byany of the following general formulae (12) to (15):

wherein in the general formula (12), R³¹ to R³⁸ each independentlyrepresent a hydrogen atom or a substituent;

wherein in the general formula (13), R⁴¹ to R⁴⁶ each independentlyrepresent a hydrogen atom or a substitutent;

wherein in the general formula (14), R⁵¹ to R⁶² each independentlyrepresent a hydrogen atom or a substituent;

wherein in the general formula (15), R⁷¹ to R⁸⁰ each independentlyrepresent a hydrogen atom on a substituent.

(10) The light-emitting material according to any one of the items (1)to (9), which contains a compound represented by the following generalformula (2):

wherein in the general formula (2), at least one of R¹¹, R¹², R¹⁴ andR¹⁵ represents a cyano group, at least three of R¹¹ to R¹⁵ eachrepresent a substituted or unsubstituted 9-carbazolyl group, asubstituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, asubstituted or unsubstituted 1-indolyl group or a substituted orunsubstituted diarylamino group, and the balance of R¹¹ to R¹⁵represents a hydroxyl group.

(11) The light-emitting material according to any one of the items (1)to (9), which contain a compound represented by the following generalformula (3):

wherein in the general formula (3), one of R⁸¹ to R⁸⁵ represents a cyanogroup, two of R⁸¹ to R⁸⁵ each represent a substituted or unsubstituted9-carbazolyl group, and the other two thereof each represent a hydrogenatom.

(12) A compound represented by the general formula (2).

(13) An organic light-emitting device containing a substrate havingthereon a light-emitting layer containing the light-emitting materialaccording to any one of the items (1) to (11).

(14) The organic light-emitting device according to the item (13), whichemits delayed fluorescent light.

(15) The organic light-emitting device according to the item (13) or(14), which is an organic electroluminescent device.

(16) A delayed fluorescent emitting having a structure represented bythe general formula (1).

Advantageous Effects of Invention

The organic light-emitting device of the invention has such a featurethat the device has a high light emission efficiency. The delayedfluorescent material of the invention has such a feature that when thematerial is need in a light-emitting layer of an organic light-emittingdevice, the organic light-emitting device emits delayed fluorescentlight with a light emission efficiency that is drastically enhanced. Thecompound of the invention is extremely useful as a light-emittingmaterial for the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic cross sectional view showing an example of a layerstructure of an organic electroluminescent device.

FIG. 2 is a time resolved spectrum of a toluene solution of the compound1 of Example 1.

FIG. 3 is a graph showing the change of the light emission lifetimedepending on temperature of the organic photoluminescent device usingthe compound 1 Example 2.

FIG. 4 is a graph showing the electric current density-voltagecharacteristics of the organic electroluminescent device using thecompound 1 of Example 1.

FIG. 5 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 1 of Example 3.

FIG. 6 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 6 of Example 4.

FIG. 7 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 301 of Example 5.

FIG. 8 is a graph showing the electric current density-voltagecharacteristics of the organic electroluminescent device using thecompound 501 of Example 6.

FIG. 9 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 501 of Example 6.

FIG. 10 is a light emission spectrum of the organic electroluminescentdevice using the compound 252 of Example 7.

FIG. 11 is a graph showing the electric current density-voltagecharacteristics of the organic electroluminescent device using thecompound 252 of Example 7.

FIG. 12 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 252 of Example 7.

FIG. 13 is a light emission spectrum of the organic electroluminescentdevice using the compound 523 of Example 8.

FIG. 14 is a graph showing the electric current density-voltagecharacteristics of the organic electroluminescent device using onecompound 523 of Example 8.

FIG. 15 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 523 of Example 8.

FIG. 16 is a light emission spectrum of the organic electroluminescentdevice using the compound 31 of Example 9.

FIG. 17 is a graph showing the electric current density-voltagecharacteristics of the organic electroluminescent device using thecompound 31 of Example 9.

FIG. 18 is a graph showing the external quantum efficiency-electriccurrent density characteristics of the organic electroluminescent deviceusing the compound 31 of Example 9.

FIG. 19 is a graph showing the luminance efficiency-luminancecharacteristics of the organic electroluminescent device using thecompound 301 of Example 10.

FIG. 20 is a graph showing the luminance deterioration characteristicsof the organic electroluminescent device using the compound 301 ofExample 10.

DESCRIPTION OF EMBODIMENTS

The contents of the invention will be described in detail below. Theconstitutional elements may be described below with reference torepresentative embodiments and specific examples of the invention, butthe invention is not limited to the embodiments and the examples. In thepresent specification, a numerical range expressed by “from X to Y”means a range including the numerals X and Y as the lower limit and theupper limit, respectively.

Compound Represented by General Formula (1)

The light-emitting material of the invention contains the compoundrepresented by the following general formula (1). The organiclight-emitting device of the invention contains the compound representedby the following general formula (1) as a light-emitting material of alight-emitting layer. The compound represented by the general formula(1) will be described.

In the general formula (1) at least one of R¹ to R⁵ represents a cyanogroup. In the case where any one thereof is a cyano group, the cyanogroup may be any of R¹ to R³. In the case where any two thereof each area cyano group, examples thereof include a combination of R¹ and R³, anda combination of R² and R⁴. In the case where any three thereof each area cyano group, examples thereof include a combination of R¹, R³ and R⁴.

In the general formula (1), at least one of R¹ to R⁵ represents a grouprepresented by the following general formula (11). In the case where twoor more thereof represent a group represented by the general formula(11), the groups may be the same as or different from each other, andare preferably the same as each other.

In the general, formula (11), R²¹ to R²⁸ each independently represent ahydrogen atom or a substituent, provided that at least one of thefollowing requirements (A) and (B) is satisfied, and both therequirements (A) and (B) are preferably satisfied:

(A) R²⁵ and R²⁶ jointly form a single bond, and

(B) R²⁷ and R²⁸ jointly form an atomic group that is required forforming a substituted or unsubstituted benzene ring.

The group represented by the general formula (11) is preferably asubstituted or unsubstituted 9-carbazolyl group, a substituted orunsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, a substituted orunsubstituted 1-indolyl group or a substituted or unsubstituteddiarylamino group. Accordingly, it is preferred that at least one of R¹to R⁵ in the general formula (1) represents a substituted orunsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group. Itis more preferred that at least two of R¹ to R⁵ in the general formula(1) represent a substituted or unsubstituted 9-carbazolyl group, asubstituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, asubstituted or unsubstituted 1-indolyl group, or a substituted orunsubstituted diarylamino group.

Preferred examples of the group represented by the general formula (11)include groups having a structure represented by any of the followinggeneral formulae (12) to (15), and more preferred examples thereofinclude groups having a structure represented by the following generalformula (12).

In the general formulae (12) to (15), R³¹ to R³⁸, R⁴¹ to R⁴⁶, R⁵¹ toR⁶², and R⁷¹ to R⁸⁰ each independently represent a hydrogen atom, or asubstituent. In the case where the group represented by the generalformulae (12) to (15) has a substituent, the substitution position andthe number of the substituent are not particularly limited. The numberof substituent of the groups is preferably from 0 to 6, more preferablyfrom 0 to 4, and for example, preferably from 0 to 2. In the case wherethe groups have plural substituents, the substituents may be the same asor different from each other, and are preferably the same as each other.

In the case where the group represented by the general formula (12) hasa substituent, any of R³² R³⁷ is preferably a substituent. Preferredexamples of the case include the case where R³² and R³⁷ aresubstituents, the case here R³³ and R³⁶ are substituents, and the casewhere R³⁴ and R³⁵ are substituents.

In the case where the group represented by the general formula (13) hasa substituent, any of R⁴² and R⁴⁶ is preferably a substituent. Preferredexamples of the case include the case where R⁴² is a substituent, andthe case where R⁴³ is a substituent.

In the case where the group represented by the general formula (14) hasa substituent, any of R⁵² to R⁶⁰ is preferably a substitutent. Preferredexamples of the case include the case where any of R⁵² to R⁵⁴ is asubstituent, and the case where any of R⁵⁵ to R⁶⁰ is a substituent.

In the case where the group represented by the general formula (15) hasa substituent, any of R⁷² to R⁷⁴ and R⁷⁷ to R⁷⁹ is preferably asubstituent. Preferred examples of the case include the case where R⁷²and R⁷⁹ are substituents, the case where R⁷³ and R⁷⁸ are substituents,the case where R⁷⁴ and R⁷⁷ are substituents, and the case where R⁷²,R⁷⁴, R⁷⁷ and R⁷⁹ are substituents. More preferred examples of the caseinclude the case where R⁷⁴ and R⁷⁷ are substituents, and the case whereR⁷², R⁷⁴, R⁷⁷ and R⁷⁹ are substituents. The substituents herein each areparticularly preferably a substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms or a substituted or unsubstituted aryl grouphaving from 6 to 40 carbon atoms, and further preferably anunsubstituted alkyl group having from 1 to 6 carbon atoms, anunsubstituted aryl group having from 6 to 10 carbon atoms, or an arylgroup having from 6 to 10 carbon atoms substituted with an aryl grouphaving from 6 to 10 carbon atoms.

Examples of the substituent that may be R²¹ to R²⁸ in the generalformula (11), R³¹ to R³⁸ in the general formula (12), R⁴¹ to R⁴⁶ in thegeneral formula (13), R⁵¹ to R⁶² in the general formula (14), and R⁷¹ toR⁸⁰ in the general formula (15) include a hydroxy group, a halogenatoms, a cyano group, an alkyl group having from 1 to 20 carbon atoms,an alkoxy group having from 1 to 20 carbon atoms, an alkylthio grouphaving 1 to 20 carbon atoms, an alkyl-substituted amino group havingfrom 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, anaryl group having from 6 to 40 carbon atoms, a heteroaryl group havingfrom 3 to 40 carbon atoms, a diarylamino group having from 12 to 40carbon atoms, a substituted or unsubstituted carbazolyl group havingfrom 12 to 40 carbon atoms, an alkenyl group having from 2 to 10 carbonatoms, an alkynyl group having from 2 to 10 carbon atoms, analkoxycarbonyl group having from 3 to 10 carbon atoms, an alkylsulfonylgroup having from 1 to 10 carbon atoms, a haloalkyl group having from 1to 10 carbon atoms, an amide group, an alkylamide group having from 2 to10 carbon atoms, a trialkylsilyl group having from 3 to 20 carbon atoms,a trialkylsilylalkyl group having from 4 to 20 carbon atoms, atrialkylsilylalkenyl group having from 5 to 20 carbon atoms, atrialkylsilylalkynyl group having from 5 to 30 carbon atoms, and a nitrogroup. In these specific examples, the groups that may be furthersubstituted with a substituent may be substituted. More preferredexamples of the substituent include a halogen atom, a cyano group, asubstituted or unsubstituted alkyl group having from 1 to 20 carbonatoms, an alkoxy group having from 1 to 30 carbon atoms, a substitutedor unsubstituted aryl group having from 6 to 40 carbon atoms, asubstituted or unsubstituted heteroaryl group having from 3 to 40 carbonatoms, a substituted or unsubstituted diarylamino group having from 12to 40 carbon atoms, and a substituted or unsubstituted carbazolyl grouphaving from 12 to 40 carbon atoms. Further preferred examples of thesubstituent include a fluorine atom, a chlorine atom, a cyano group, asubstituted or unsubstituted alkyl group having from 1 to 10 carbonatoms, a substituted or unsubstituted alkoxy group having from 1 to 10carbon atoms, a substituted or unsubstituted dialkylamino group havingfrom 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving from 6 to 15 carbon atoms, and a substituted or unsubstitutedheteroaryl group having from 3 to 12 carbon atoms.

The alkyl group referred in the description may be any of linear,branched or cyclic and more preferably has from 1 to 6 carbon atoms, andspecific examples thereof include a methyl group, an ethyl group, apropyl group, a butyl group, a t-butyl group, a pentyl group, a hexylgroup and an isopropyl group. The aryl group may be a monocyclic ring ora fused ring, and specific examples thereof include a phenyl group and anaphthyl group. The alkoxy group may be any of linear, branched orcyclic and more preferably has from 1 to 6 carbon atoms, and specificexamples thereof include a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, a t-butoxy group, a pentyloxy group, a hexyloxygroup and an isopropoxy group. The two alkyl groups of the dialkylaminogroup may be the same as or different from each other, and arepreferably the same as each other. The two alkyl groups of thedialkylamino group each may independently be any of linear, branched orcyclic and each independently preferably have from 1 to 6 carbon atoms,and specific examples thereof include a methyl group an ethyl group, apropyl group, a butyl group, a pentyl group, a hexyl group and anisopropyl group. The aryl group may be a monocyclic ring or a fusedring, and specific examples thereof include a phenyl group and anaphthyl group. The heteroaryl group may also be a monocyclic ring or afused ring, and specific examples thereof include a pyridyl group, apyridazyl group, a pyrimidyl group, a triazyl group, a triazolyl groupand a benzotriazolyl group. The heteroaryl group may be a group that isbonded through the heteroatom or a group that is bonded through thecarbon atom constituting the heteroaryl ring.

In the general formula (1), in the case where any one of R¹ to R⁵represents a group represented by the general formula (11), the grouprepresented by the general formula (11) may be any of R¹ to R³. In thecase where two thereof each are a group represented by the generalformula (11), examples of the case include a combination of R¹ and R³,and a combination of R² and R⁴. In the case where three thereof each area group represented by the general formula (11), examples of the caseinclude a combination of R¹, R³ and R⁴.

Any one of the two o-positions of the benzene ring with respect to thegroup represented by the general formula (11) bonded thereto ispreferably a cyan group. Both the two o-positions may be cyano groups.In the case where two or more groups represented by the general formula(11) are bonded to the benzene ring, at least two thereof preferablysatisfy the requirement that any one of the two o-positions of thebenzene ring with respect to the group represented by the generalformula (11) bonded thereto is a cyano group.

In the general formula (1), at least one of R¹ to R⁵ represents a cyanogroup, at least one of R¹ to R⁵ represents a group represented by thefollowing general formula (11), and the balance of R¹ to R⁵ represents ahydrogen atom or a substituent.

Examples of the preferred substituent that may be R¹ to R⁵ include ahydroxy group, a halogen atom, an alkyl group having from 1 to 20 carbonatoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio grouphaving from 1 to 20 carbon atoms, an alkyl-substituted amino grouphaving from 1 to 20 carbon atoms, an acyl group having from 2 to 20carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroarylgroup having from 3 to 40 carbon atoms, an alkenyl group having from 2to 10 carbon atoms, an alkynyl group having from 2 to 10 carbon atoms,an alkoxycarbonyl group having from 2 to 10 carbon atoms, analkylsulfonyl group having from 1 to 10 carbon atoms, an amide group, analkylamide group having from 2 to 10 carbon atoms, a trialkylsilyl grouphaving from 3 to 20 carbon atoms, a trialkylsilylalkyl group having from4 to 20 carbon atoms, a trialkylsilylalkenyl group having from 5 to 20carbon atoms, a trialkylsilylalkynyl group having from 5 to 20 carbonatoms, and a nitro group. In these specific examples, the groups thatmay be further substituted with a substituent may be substituted. Morepreferred examples of the substituent include a hydroxy group, a halogenatom, a substituted or unsubstituted alkyl group having from 1 to 20carbon atoms, as alkoxy group having from 1 to 20 carbon atoms, asubstituted or unsubstituted dialkylamino group having from 1 to 20carbon atoms, a substituted or unsubstituted aryl group having from 6 to40 carbon atoms, and a substituted or unsubstituted heteroaryl grouphaving from 3 to 40 carbon atoms. Further preferred examples of thesubstituent include a hydroxy group, a fluorine atom, a chlorine atom, asubstituted or unsubstituted alkyl group having from 1 to 10 carbonatoms, a substituted or unsubstituted alkoxy group having from 1 to 10carbon atoms, a substituted or unsubstituted dialkylamino group havingfrom 1 to 10 carbon atoms, a substituted or unsubstituted aryl grouphaving from 6 to 15 carbon atoms, and a substituted or unsubstitutedheteroaryl group having from 3 to 12 carbon atoms. Still furtherpreferred examples of the substituent include a hydroxy group, afluorine atom, and a chlorine atom.

In the general formula (1), the number of hydrogen atom of R¹ to R⁵ ispreferably 3 or less, more preferably 2 or less, further preferably 1 orless, and still further preferably 0.

Preferred examples of the combination of R¹ to R⁵ in the general formula(1) include the case where at least one of R¹ to R⁵ represents a cyanogroup, and the balance of R¹ to R⁵ each independently represents ahydroxy group, a halogen atom, a substituted or unsubstituted9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group.Preferred examples of the combination also include the case where atleast one of R¹ to R⁵ represents a cyano group, and the balance of R¹ toR⁵ each independently represents a substituted or unsubstituted9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group.Preferred examples of the combination further include the case where atleast one or R¹ to R⁵ in the general formula (1) represents a cyanogroup, and the balance of R¹ to R⁵ each independently represents any ofa hydroxy group, a halogen atom or a substituted or unsubstituted9-carbazolyl group. Preferred examples of the combination still furtherinclude the case where at least one of R¹ to R⁵ in the general formula(1) represents a cyano group, and the balance of R¹ to R⁵ eachrepresents a substituted or unsubstituted 9-carbazolyl group. Preferredexamples of the combination still further include the case where atleast one of R¹ to R⁵ in the general formula (1) represents a cyanogroup, at least one of R¹ to R⁵ represents a hydroxy group, and thebalance of R¹ to R⁵ each represents a substituted or unsubstituted9-carbazolyl group. Preferred examples of the combination still furtherinclude the case where at least one of R¹ to R⁵ in the general formula(1) represents a cyano group, at least one of R¹ to R⁵ represents ahalogen atom, and the balance of R¹ to R⁵ each represents a substitutedor unsubstituted 9-carbazolyl group.

Specific examples of the compound represents by the general formula (1)will be shown below, but the compound represented by the general formula(1) capable of being used in the invention is not construed as beinglimited to the specific examples. In the following specific examples ofthe compound, in the case where two or more groups represented by any ofthe general formulae (12) to (15) are present in the molecule, all thegroups are the same structure as each other. For example, in thecompound 1 in Table 1, R¹, R², R⁴ and R⁵ in the general formula (1) arethe groups represented by the general formula (12), and all the groupsare unsubstituted 9-carbazolyl groups.

TABLE 1 Compound General Formula (1) General Formula (12) No. R¹ R² R³R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 1 General General CN GeneralGeneral H H H H Formula (12) Formula (12) Formula (12) Formula (12) 2General General CN General General H CH₃ H H Formula (12) Formula (12)Formula (12) Formula (12) 3 General General CN General General H CH₃O HH H Formula (12) Formula (12) Formula (12) Formula (12) 4 GeneralGeneral CN General General H H CH₃ H Formula (12) Formula (12) Formula(12) Formula (12) 5 General General CN General General H H CH₃O HFormula (12) Formula (12) Formula (12) Formula (12) 6 General General CNGeneral General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12)Formula (12) 7 General General CN General General H H Cl H Formula (12)Formula (12) Formula (12) Formula (12) 8 General General CN GeneralGeneral H H F H Formula (12) Formula (12) Formula (12) Formula (12) 9General General CN General General H H H CH₃ Formula (12) Formula (12)Formula (12) Formula (12) 10 General General CN General General H H HCH₃O Formula (12) Formula (12) Formula (12) Formula (12) 11 GeneralGeneral CN General H H H H H Formula (12) Formula (12) Formula (12) 12General General CN General H H CH₃ H H Formula (12) Formula (12) Formula(12) 13 General General CN General H H CH₃O H H Formula (12) Formula(12) Formula (12) 14 General General CN General H H H CH₃ H Formula (12)Formula (12) Formula (12) 15 General General CN General H H H CH₃O HFormula (12) Formula (12) Formula (12) 16 General General CN General H HH t-C₄H₉ H Formula (12) Formula (12) Formula (12) 17 General General CNGeneral H H H Cl H Formula (12) Formula (12) Formula (12) 18 GeneralGeneral CN General H H H F H Formula (12) Formula (12) Formula (12) 19General General CN General H H H H CH₃ Formula (12) Formula (12) Formula(12) 20 General General CN General H H H H CH₃O Formula (12) Formula(12) Formula (12) 21 General General CN H H H H H H Formula (12) Formula(12) 22 General General CN H H H CH₃ H H Formula (12) Formula (12) 23General General CN H H H CH₃O H H Formula (12) Formula (12) 24 GeneralGeneral CN H H H H CH₃ H Formula (12) Formula (12) 25 General General CNH H H H CH₃O H Formula (12) Formula (12) 26 General General CN H H H Ht-C₄H₉ H Formula (12) Formula (12) 27 General General CN H H H H Cl HFormula (12) Formula (12) 28 General General CN H H H H F H Formula (12)Formula (12) 29 General General CN H H H H H CH₃ Formula (12) Formula(12) 30 General General CN H H H H H CH₃O Formula (12) Formula (12) 31General H CN General H H H H H Formula (12) Formula (12) 32 General H CNGeneral H H CH₃ H H Formula (12) Formula (12) 33 General H CN General HH CH₃O H H Formula (12) Formula (12) 34 General H CN General H H H CH₃ HFormula (12) Formula (12) 35 General H CN General H H H CH₃O H Formula(12) Formula (12) 36 General H CN General H H H t-C₄H₉ H Formula (12)Formula (12) 37 General H CN General H H H Cl H Formula (12) Formula(12) 38 General H CN General H H H F H Formula (12) Formula (12) 39General H CN General H H H H CH₃ Formula (12) Formula (12) 40 General HCN General H H h H CH₃O Formula (12) Formula (12) 41 General H CNGeneral General H H H H Formula (12) Formula (12) Formula (12) 42General H CN H General H CH₃ H H Formula (12) Formula (12) 43 General HCN H General H CH₃O H H Formula (12) Formula (12) 44 General H CN HGeneral H H CH₃ H Formula (12) Formula (12) 45 General H CN H General HH CH₃O H Formula (12) Formula (12) 46 General H CN H General H H t-C₄H₉H Formula (12) Formula (12) 47 General H CN H General H H Cl H Formula(12) Formula (12) 48 General H CN H General H H F H Formula (12) Formula(12) 49 General H CN H General H H H CH₃ Formula (12) Formula (12) 50General H CN H General H H H CH₃O Formula (12) Formula (12) 51 General HCN H H H H H H Formula (12) 52 General H CN H H H CH₃ H H Formula (12)53 General H CN H H H CH₃O H H Formula (12) 54 General H CN H H H H CH₃H Formula (12) 55 General H CN H H H H CH₃O H Formula (12) 56 General HCN H H H H t-C₄H₉ H Formula (12) 57 General H CN H H H H Cl H Formula(12) 58 General H CN H H H H F H Formula (12) 59 General H CN H H H H HCH₃ Formula (12) 60 General H CN H H H H H CH₃O Formula (12) 61 GeneralGeneral CN General F H H H H Formula (12) Formula (12) Formula (12) 62General General CN General F H CH₃ H H Formula (12) Formula (12) Formula(12) 63 General General CN General F H CH₃O H H Formula (12) Formula(12) Formula (12) 64 General General CN General F H H CH₃ H Formula (12)Formula (12) Formula (12) 65 General General CN General F H H CH₃O HFormula (12) Formula (12) Formula (12) 66 General General CN General F HH t-C₄H₉ H Formula (12) Formula (12) Formula (12) 67 General General CNGeneral F H H Cl H Formula (12) Formula (12) Formula (12) 68 GeneralGeneral CN General F H H F H Formula (12) Formula (12) Formula (12) 69General General CN General F H H H CH₃ Formula (12) Formula (12) Formula(12) 70 General General CN General F H H H CH₃O Formula (12) Formula(12) Formula (12) 71 General General CN F F H H H H Formula (12) Formula(12) 72 General General CN F F H CH₃ H H Formula (12) Formula (12) 73General General CN F F H CH₃O H H Formula (12) Formula (12) 74 GeneralGeneral CN F F H H CH₃ H Formula (12) Formula (12) 75 General General CNF F H H CH₃O H Formula (12) Formula (12) 76 General General CN F F H Ht-C₄H₉ H Formula (12) Formula (12) 77 General General CN F F H H Cl HFormula (12) Formula (12) 78 General General CN F F H H F H Formula (12)Formula (12) 79 General General CN F F H H H CH₃ Formula (12) Formula(12) 80 General General CN F F H H H CH₃O Formula (12) Formula (12) 81General F CN General F H H H H Formula (12) Formula (12) 82 General F CNGeneral F H CH₃ H H Formula (12) Formula (12) 83 General F CN General FH CH₃O H H Formula (12) Formula (12) 84 General F CN General F H H CH₃ HFormula (12) Formula (12) 85 General F CN General F H H CH₃O H Formula(12) Formula (12) 86 General F CN General F H H t-C₄H₉ H Formula (12)Formula (12) 87 General F CN General F H H Cl H Formula (12) Formula(12) 88 General F CN General F H H F H Formula (12) Formula (12) 89General F CN General F H H H CH₃ Formula (12) Formula (12) 90 General FCN General F H H H CH₃O Formula (12) Formula (12) 91 General F CN FGeneral H H H H Formula (12) Formula (12) 92 General F CN F General HCH₃ H H Formula (12) Formula (12) 93 General F CN F General H CH₃O H HFormula (12) Formula (12) 94 General F CN F General H H CH₃ H Formula(12) Formula (12) 95 General F CN F General H H CH₃O H Formula (12)Formula (12) 96 General F CN F General H H t-C₄H₉ H Formula (12) Formula(12) 97 General F CN F General H H Cl H Formula (12) Formula (12) 98General F CN F General H H F H Formula (12) Formula (12) 99 General F CNF General H H H CH₃ Formula (12) Formula (12) 100 General F CN F GeneralH H H CH₃O Formula (12) Formula (12) 101 General F CN F F H H H HFormula (12) 102 General F CN F F H CH₃ H H Formula (12) 103 General FCN F F H CH₃O H H Formula (12) 104 General F CN F F H H CH₃ H Formula(12) 105 General F CN F F H H CH₃O H Formula (12) 106 General F CN F F HH t-C₄H₉ H Formula (12) 107 General F CN F F H H Cl H Formula (12) 108General F CN F F H H F H Formula (12) 109 General F CN F F H H H CH₃Formula (12) 110 General F CN F F H H H CH₃O Formula (12) 111 GeneralGeneral CN General OH H H H H Formula (12) Formula (12) Formula (12) 112General General CN General OH H CH₃ H H Formula (12) Formula (12)Formula (12) 113 General General CN General OH H CH₃O H H Formula (12)Formula (12) Formula (12) 114 General General CN General OH H H CH₃ HFormula (12) Formula (12) Formula (12) 115 General General CN General OHH H CH₃O H Formula (12) Formula (12) Formula (12) 116 General General CNGeneral OH H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 117General General CN General OH H H Cl H Formula (12) Formula (12) Formula(12) 118 General General CN General OH H H F H Formula (12) Formula (12)Formula (12) 119 General General CN General OH H H H CH₃ Formula (12)Formula (12) Formula (12) 120 General General CN General OH H H H CH₃OFormula (12) Formula (12) Formula (12) 121 General General CN OH OH H HH H Formula (12) Formula (12) 122 General General CN OH OH H CH₃ H HFormula (12) Formula (12) 123 General General CN OH OH H CH₃O H HFormula (12) Formula (12) 124 General General CN OH OH H H CH₃ H Formula(12) Formula (12) 125 General General CN OH OH H H CH₃O H Formula (12)Formula (12) 126 General General CN OH OH H H t-C₄H₉ H Formula (12)Formula (12) 127 General General CN OH OH H H Cl H Formula (12) Formula(12) 128 General General CN OH OH H H F H Formula (12) Formula (12) 129General General CN OH OH H H H CH₃ Formula (12) Formula (12) 130 GeneralGeneral CN OH OH H H H CH₃O Formula (12) Formula (12) 131 General OH CNGeneral OH H H H H Formula (12) Formula (12) 132 General OH CN GeneralOH H CH₃ H H Formula (12) Formula (12) 133 General OH CN General OH HCH₃O H H Formula (12) Formula (12) 134 General OH CN General OH H H CH₃H Formula (12) Formula (12) 135 General OH CN General OH H H CH₃O HFormula (12) Formula (12) 136 General OH CN General OH H H t-C₄H₉ HFormula (12) Formula (12) 137 General OH CN General OH H H Cl H Formula(12) Formula (12) 138 General OH CN General OH H H F H Formula (12)Formula (12) 139 General OH CN General OH H H H CH₃ Formula (12) Formula(12) 140 General OH CN General OH H H H CH₃O Formula (12) Formula (12)141 General OH CN OH General H H H H Formula (12) Formula (12) 142General OH CN OH General H CH₃ H H Formula (12) Formula (12) 143 GeneralOH CN OH General H CH₃O H H Formula (12) Formula (12) 144 General OH CNOH General H H CH₃ H Formula (12) Formula (12) 145 General OH CN OHGeneral H H CH₃O H Formula (12) Formula (12) 146 General OH CN OHGeneral H H t-C₄H₉ H Formula (12) Formula (12) 147 General OH CN OHGeneral H H Cl H Formula (12) Formula (12) 148 General OH CN OH GeneralH H F H Formula (12) Formula (12) 149 General OH CN OH General H H H CH₃Formula (12) Formula (12) 150 General OH CN OH General H H H CH₃OFormula (12) Formula (12) 151 General OH CN OH OH H H H H Formula (12)152 General OH CN OH OH H CH₃ H H Formula (12) 153 General OH CN OH OH HCH₃O H H Formula (12) 154 General OH CN OH OH H H CH₃ H Formula (12) 155General OH CN OH OH H H CH₃O H Formula (12) 156 General OH CN OH OH H Ht-C₄H₉ H Formula (12) 157 General OH CN OH OH H H Cl H Formula (12) 158General OH CN OH OH H H F H Formula (12) 159 General OH CN OH OH H H HCH₃ Formula (12) 160 General OH CN OH OH H H H CH₃O Formula (12) 161General General CN General Cl H H H H Formula (12) Formula (12) Formula(12) 162 General General CN General Cl H CH₃ H H Formula (12) Formula(12) Formula (12) 163 General General CN General Cl H CH₃O H H Formula(12) Formula (12) Formula (12) 164 General General CN General Cl H H CH₃H Formula (12) Formula (12) Formula (12) 165 General General CN GeneralCl H H CH₃O H Formula (12) Formula (12) Formula (12) 166 General GeneralCN General Cl H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 167General General CN General Cl H H Cl H Formula (12) Formula (12) Formula(12) 168 General General CN General Cl H H H H Formula (12) Formula (12)Formula (12) 169 General General CN General Cl H H H CH₃ Formula (12)Formula (12) Formula (12) 170 General General CN General Cl H H H CH₃OFormula (12) Formula (12) Formula (12) 171 General General CN General FH H H H Formula (12) Formula (12) Formula (12) 172 General General CNGeneral F H CH₃ H H Formula (12) Formula (12) Formula (12) 173 GeneralGeneral CN General F H CH₃O H H Formula (12) Formula (12) Formula (12)174 General General CN General F H H CH₃ H Formula (12) Formula (12)Formula (12) 175 General General CN General F H H CH₃O H Formula (12)Formula (12) Formula (12) 176 General General CN General F H H t-C₄H₉ HFormula (12) Formula (12) Formula (12) 177 General General CN General FH H Cl H Formula (12) Formula (12) Formula (12) 178 General General CNGeneral F H H F H Formula (12) Formula (12) Formula (12) 179 GeneralGeneral CN General F H H H CH₃ Formula (12) Formula (12) Formula (12)180 General General CN General F H H H CH₃O Formula (12) Formula (12)Formula (12) 181 General General CN General CH₃O H H H H Formula (12)Formula (12) Formula (12) 182 General General CN General CH₃O H CH₃ H HFormula (12) Formula (12) Formula (12) 183 General General CN GeneralCH₃O H CH₃O H H Formula (12) Formula (12) Formula (12) 184 GeneralGeneral CN General CH₃O H H CH₃ H Formula (12) Formula (12) Formula (12)185 General General CN General CH₃O H H CH₃O H Formula (12) Formula (12)Formula (12) 186 General General CN General CH₃O H H t-C₄H₉ H Formula(12) Formula (12) Formula (12) 187 General General CN General CH₃O H HCl H Formula (12) Formula (12) Formula (12) 188 General General CNGeneral CH₃O H H F H Formula (12) Formula (12) Formula (12) 189 GeneralGeneral CN General C₂H₅O H H H CH₃ Formula (12) Formula (12) Formula(12) 190 General General CN General C₂H₅O H H H CH₃O Formula (12)Formula (12) Formula (12) 191 General General CN General C₂H₅O H H H HFormula (12) Formula (12) Formula (12) 192 General General CN GeneralC₂H₅O H CH₃ H H Formula (12) Formula (12) Formula (12) 193 GeneralGeneral CN General C₂H₅O H CH₃O H H Formula (12) Formula (12) Formula(12) 194 General General CN General C₂H₅O H H CH₃ H Formula (12) Formula(12) Formula (12) 195 General General CN General C₂H₅O H H CH₃O HFormula (12) Formula (12) Formula (12) 196 General General CN GeneralC₂H₅O H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 197 GeneralGeneral CN General C₂H₅O H H Cl H Formula (12) Formula (12) Formula (12)198 General General CN General C₂H₅O H H F H Formula (12) Formula (12)Formula (12) 199 General General CN General C₂H₅O H H H CH₃ Formula (12)Formula (12) Formula (12) 200 General General CN General C₂H₅O H H HCH₃O Formula (12) Formula (12) Formula (12) 201 General General CNGeneral C₆H₅O H H H H Formula (12) Formula (12) Formula (12) 202 GeneralGeneral CN General C₆H₅O H CH₃ H H Formula (12) Formula (12) Formula(12) 203 General General CN General C₆H₅O H CH₃O H H Formula (12)Formula (12) Formula (12) 204 General General CN General C₆H₅O H H CH₃ HFormula (12) Formula (12) Formula (12) 205 General General CN GeneralC₆H₅O H H CH₃O H Formula (12) Formula (12) Formula (12) 206 GeneralGeneral CN General C₆H₅O H H t-C₄H₉ H Formula (12) Formula (12) Formula(12) 207 General General CN General C₆H₅O H H Cl H Formula (12) Formula(12) Formula (12) 208 General General CN General C₆H₅O H H F H Formula(12) Formula (12) Formula (12) 209 General General CN General C₆H₅O H HH CH₃ Formula (12) Formula (12) Formula (12) 210 General General CNGeneral C₆H₅O H H H CH₃O Formula (12) Formula (12) Formula (12) 211General General CN General Formula (21) H H H H Formula (12) Formula(12) Formula (12) 212 General General CN General Formula (21) H CH₃ H HFormula (12) Formula (12) Formula (12) 213 General General CN GeneralFormula (21) H CH₃O H H Formula (12) Formula (12) Formula (12) 214General General CN General Formula (21) H H CH₃ H Formula (12) Formula(12) Formula (12) 215 General General CN General Formula (21) H H CH₃O HFormula (12) Formula (12) Formula (12) 216 General General CN GeneralFormula (21) H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 217General General CN General Formula (21) H H Cl H Formula (12) Formula(12) Formula (12) 218 General General CN General Formula (21) H H F HFormula (12) Formula (12) Formula (12) 219 General General CN GeneralFormula (21) H H H CH₃ Formula (12) Formula (12) Formula (12) 220General General CN General Formula (21) H H H CH₃O Formula (12) Formula(12) Formula (12) 221 General General CN General Formula (22) H H H HFormula (12) Formula (12) Formula (12) 222 General General CN GeneralFormula (22) H CH₃ H H Formula (12) Formula (12) Formula (12) 223General General CN General Formula (22) H CH₃O H H Formula (12) Formula(12) Formula (12) 224 General General CN General Formula (22) H H CH₃ HFormula (12) Formula (12) Formula (12) 225 General General CN GeneralFormula (22) H H CH₃O H Formula (12) Formula (12) Formula (12) 226General General CN General Formula (22) H H t-C₄H₉ H Formula (12)Formula (12) Formula (12) 227 General General CN General Formula (22) HH Cl H Formula (12) Formula (12) Formula (12) 228 General General CNGeneral Formula (22) H H F H Formula (12) Formula (12) Formula (12) 229General General CN General Formula (22) H H H CH₃ Formula (12) Formula(12) Formula (12) 230 General General CN General Formula (22) H H H CH₃OFormula (12) Formula (12) Formula (12) 231 General General CN GeneralFormula (23) H H H H Formula (12) Formula (12) Formula (12) 232 GeneralGeneral CN General Formula (23) H CH₃ H H Formula (12) Formula (12)Formula (12) 233 General General CN General Formula (23) H CH₃O H HFormula (12) Formula (12) Formula (12) 234 General General CN GeneralFormula (23) H H CH₃ H Formula (12) Formula (12) Formula (12) 235General General CN General Formula (23) H H CH₃O H Formula (12) Formula(12) Formula (12) 236 General General CN General Formula (23) H H t-C₄H₉H Formula (12) Formula (12) Formula (12) 237 General General CN GeneralFormula (23) H H Cl H Formula (12) Formula (12) Formula (12) 238 GeneralGeneral CN General Formula (23) H H F H Formula (12) Formula (12)Formula (12) 239 General General CN General Formula (23) H H H CH₃Formula (12) Formula (12) Formula (12) 240 General General CN GeneralFormula (23) H H H CH₃O Formula (12) Formula (12) Formula (12) 241General General CN General Formula (24) H H H H Formula (12) Formula(12) Formula (12) 242 General General CN General Formula (24) H CH₃ H HFormula (12) Formula (12) Formula (12) 243 General General CN GeneralFormula (24) H CH₃O H H Formula (12) Formula (12) Formula (12) 244General General CN General Formula (24) H H CH₃ H Formula (12) Formula(12) Formula (12) 245 General General CN General Formula (24) H H CH₃O HFormula (12) Formula (12) Formula (12) 246 General General CN GeneralFormula (24) H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 247General General CN General Formula (24) H H Cl H Formula (12) Formula(12) Formula (12) 248 General General CN General Formula (24) H H F HFormula (12) Formula (12) Formula (12) 249 General General CN GeneralFormula (24) H H H CH₃ Formula (12) Formula (12) Formula (12) 250General General CN General Formula (24) H H H CH₃O Formula (12) Formula(12) Formula (12) 251 General General CN General General H C₆H₅ H HFormula (12) Formula (12) Formula (12) Formula (12) 252 General GeneralCN General General H H C₆H₅ H Formula (12) Formula (12) Formula (12)Formula (12) 253 General General CN General H H C₆H₅ H H Formula (12)Formula (12) Formula (12) 254 General General CN General H H H C₆H₅ HFormula (12) Formula (12) Formula (12) 255 General General CN H H H C₆H₅H H Formula (12) Formula (12) 256 General General CN H H H H C₆H₅ HFormula (12) Formula (12) 257 General H CN General H H C₆H₅ H H Formula(12) Formula (12) 258 General H CN General H H H C₆H₅ H Formula (12)Formula (12) 259 General H CN H General H C₆H₅ H H Formula (12) Formula(12) 260 General H CN H General H H C₆H₅ H Formula (12) Formula (12) 261General H CN H H H C₆H₅ H H Formula (12) 262 General H CN H H H H C₆H₅ HFormula (12) 263 General General CN General F H C₆H₅ H H Formula (12)Formula (12) Formula (12) 264 General General CN General F H H C₆H₅ HFormula (12) Formula (12) Formula (12) 265 General General CN F F H C₆H₅H H Formula (12) Formula (12) 266 General General CN F F H H C₆H₅ HFormula (12) Formula (12) 267 General F CN General F H C₆H₅ H H Formula(12) Formula (12) 268 General F CN General F H H C₆H₅ H Formula (12)Formula (12) 269 General F CN F General H C₆H₅ H H Formula (12) Formula(12) 270 General F CN F General H H C₆H₅ H Formula (12) Formula (12) 271General F CN F F H C₆H₅ H H Formula (12) 272 General F CN F F H H C₆H₅ HFormula (12) 273 General General CN General OH H C₆H₅ H H Formula (12)Formula (12) Formula (12) 274 General General CN General OH H H C₆H₅ HFormula (12) Formula (12) Formula (12) 275 General General CN OH OH HC₆H₅ H H Formula (12) Formula (12) 276 General General CN OH OH H H C₆H₅H Formula (12) Formula (12) 277 General OH CN General OH H C₆H₅ H HFormula (12) Formula (12) 278 General OH CN General OH H H C₆H₅ HFormula (12) Formula (12) 279 General OH CN OH General H C₆H₅ H HFormula (12) Formula (12) 280 General OH CN OH General H H C₆H₅ HFormula (12) Formula (12) 281 General OH CN OH OH H C₆H₅ H H Formula(12) 282 General OH CN OH OH H H C₆H₅ H Formula (12) 283 General GeneralCN General Cl H C₆H₅ H H Formula (12) Formula (12) Formula (12) 284General General CN General Cl H H C₆H₅ H Formula (12) Formula (12)Formula (12) 285 General General CN General F H C₆H₅ H H Formula (12)Formula (12) Formula (12) 286 General General CN General F H H C₆H₅ HFormula (12) Formula (12) Formula (12) 287 General General CN GeneralCH₃O H C₆H₅ H H Formula (12) Formula (12) Formula (12) 288 GeneralGeneral CN General CH₃O H H C₆H₅ H Formula (12) Formula (12) Formula(12) 289 General General CN General C₂H₅O H C₆H₅ H H Formula (12)Formula (12) Formula (12) 290 General General CN General C₂H₅O H H C₆H₅H Formula (12) Formula (12) Formula (12) 291 General General CN GeneralC₆H₅O H C₆H₅ H H Formula (12) Formula (12) Formula (12) 292 GeneralGeneral CN General C₆H₅O H H C₆H₅ H Formula (12) Formula (12) Formula(12) 293 General General CN General Formula (21) H C₆H₅ H H Formula (12)Formula (12) Formula (12) 294 General General CN General Formula (21) HH C₆H₅ H Formula (12) Formula (12) Formula (12) 295 General General CNGeneral Formula (22) H C₆H₅ H H Formula (12) Formula (12) Formula (12)296 General General CN General Formula (22) H H C₆H₅ H Formula (12)Formula (12) Formula (12) 297 General General CN General Formula (23) HC₆H₅ H H Formula (12) Formula (12) Formula (12) 298 General General CNGeneral Formula (23) H H C₆H₅ H Formula (12) Formula (12) Formula (12)299 General General CN General Formula (24) H C₆H₅ H H Formula (12)Formula (12) Formula (12) 300 General General CN General Formula (24) HH C₆H₅ H Formula (12) Formula (12) Formula (12)

TABLE 2 Compound General Formula (1) General Formula (12) No. R¹ R² R³R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 301 General CN General GeneralGeneral H H H H Formula (12) Formula (12) Formula (12) Formula (12) 302General CN General General General H CH₃ H H Formula (12) Formula (12)Formula (12) Formula (12) 303 General CN General General General H CH₃OH H Formula (12) Formula (12) Formula (12) Formula (12) 304 General CNGeneral General General H H CH₃ H Formula (12) Formula (12) Formula (12)Formula (12) 305 General CN General General General H H CH₃O H Formula(12) Formula (12) Formula (12) Formula (12) 306 General CN GeneralGeneral General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12)Formula (12) 307 General CN General General General H H Cl H Formula(12) Formula (12) Formula (12) Formula (12) 308 General CN GeneralGeneral General H H F H Formula (12) Formula (12) Formula (12) Formula(12) 309 General CN General General General H H H CH₃ Formula (12)Formula (12) Formula (12) Formula (12) 310 General CN General GeneralGeneral H H H CH₃O Formula (12) Formula (12) Formula (12) Formula (12)311 General CN General General H H H H H Formula (12) Formula (12)Formula (12) 312 General CN General General H H H CH₃ H Formula (12)Formula (12) Formula (12) 313 General CN General General H H H CH₃O HFormula (12) Formula (12) Formula (12) 314 General CN General H GeneralH H H H Formula (12) Formula (12) Formula (12) 315 General CN General HGeneral H H CH₃ H Formula (12) Formula (12) Formula (12) 316 General CNGeneral H General H H CH₃O H Formula (12) Formula (12) Formula (12) 317General CN H General General H H H H Formula (12) Formula (12) Formula(12) 318 General CN H General General H H CH₃ H Formula (12) Formula(12) Formula (12) 319 General CN H General General H H CH₃O H Formula(12) Formula (12) Formula (12) 320 H CN General General General H H H HFormula (12) Formula (12) Formula (12) 321 H CN General General GeneralH H CH₃ H Formula (12) Formula (12) Formula (12) 322 H CN GeneralGeneral General H H CH₃O H Formula (12) Formula (12) Formula (12) 323General CN General H H H H H H Formula (12) Formula (12) 324 General CNGeneral H H H H CH₃ H Formula (12) Formula (12) 325 General CN General HH H H CH₃O H Formula (12) Formula (12) 326 General CN H General H H H HH Formula (12) Formula (12) 327 General CN H General H H H CH₃ H Formula(12) Formula (12) 328 General CN H General H H H CH₃O H Formula (12)Formula (12) 329 H CN General General H H H H H Formula (12) Formula(12) 330 H CN General General H H H CH₃ H Formula (12) Formula (12) 331H CN General General H H H CH₃O H Formula (12) Formula (12) 332 GeneralCN H H General H H H H Formula (12) Formula (12) 333 General CN H HGeneral H H CH₃ H Formula (12) Formula (12) 334 General CN H H General HH CH₃O H Formula (12) Formula (12) 335 H CN General H General H H H HFormula (12) Formula (12) 336 H CN General H General H H CH₃ H Formula(12) Formula (12) 337 H CN General H General H H CH₃O H Formula (12)Formula (12) 338 H CN H General General H H H H Formula (12) Formula(12) 339 H CN H General General H H CH₃ H Formula (12) Formula (12) 340H CN H General General H H CH₃O H Formula (12) Formula (12) 341 GeneralCN H H H H H H H Formula (12) 342 General CN H H H H H CH₃ H Formula(12) 343 General CN H H H H H CH₃O H Formula (12) 344 H CN General H H HH H H Formula (12) 345 H CN General H H H H CH₃ H Formula (12) 346 H CNGeneral H H H H CH₃O H Formula (12) 347 H CN H General H H H H H Formula(12) 348 H CN H General H H H CH₃ H Formula (12) 349 H CN H General H HH CH₃O H Formula (12) 350 General CN General General F H H H H Formula(12) Formula (12) Formula (12) 351 General CN General General F H H CH₃H Formula (12) Formula (12) Formula (12) 352 General CN General GeneralF H H CH₃O H Formula (12) Formula (12) Formula (12) 353 General CNGeneral F General H H H H Formula (12) Formula (12) Formula (12) 354General CN General F General H H CH₃ H Formula (12) Formula (12) Formula(12) 355 General CN General F General H H CH₃O H Formula (12) Formula(12) Formula (12) 356 General CN F General General H H H H Formula (12)Formula (12) Formula (12) 357 General CN F General General H H CH₃ HFormula (12) Formula (12) Formula (12) 358 General CN F General GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 359 F CN GeneralGeneral General H H H H Formula (12) Formula (12) Formula (12) 360 F CNGeneral General General H H CH₃ H Formula (12) Formula (12) Formula (12)361 F CN General General General H H CH₃O H Formula (12) Formula (12)Formula (12) 362 General CN General F F H H H H Formula (12) Formula(12) 363 General CN General F F H H CH₃ H Formula (12) Formula (12) 364General CN General F F H H CH₃O H Formula (12) Formula (12) 365 GeneralCN F General F H H H H Formula (12) Formula (12) 366 General CN FGeneral F H H CH₃ H Formula (12) Formula (12) 367 General CN F General FH H CH₃O H Formula (12) Formula (12) 368 F CN General General F H H H HFormula (12) Formula (12) 369 F CN General General F H H CH₃ H Formula(12) Formula (12) 370 F CN General General F H H CH₃O H Formula (12)Formula (12) 371 General CN F F General H H H H Formula (12) Formula(12) 372 General CN F F General H H CH₃ H Formula (12) Formula (12) 373General CN F F General H H CH₃O H Formula (12) Formula (12) 374 F CNGeneral F General H H H H Formula (12) Formula (12) 375 F CN General FGeneral H H CH₃ H Formula (12) Formula (12) 376 F CN General F General HH CH₃O H Formula (12) Formula (12) 377 F CN F General General H H H HFormula (12) Formula (12) 378 F CN F General General H H CH₃ H Formula(12) Formula (12) 379 F CN F General General H H CH₃O H Formula (12)Formula (12) 380 General CN F F F H H H H Formula (12) 381 General CN FF F H H CH₃ H Formula (12) 382 General CN F F F H H CH₃O H Formula (12)383 F CN General F F H H H H Formula (12) 384 F CN General F F H H CH₃ HFormula (12) 385 F CN General F F H H CH₃O H Formula (12) 386 F CN FGeneral F H H H H Formula (12) 387 F CN F General F H H CH₃ H Formula(12) 388 F CN F General F H H CH₃O H Formula (12) 389 General CN GeneralGeneral OH H H H H Formula (12) Formula (12) Formula (12) 390 General CNGeneral General OH H H CH₃ H Formula (12) Formula (12) Formula (12) 391General CN General General OH H H CH₃O H Formula (12) Formula (12)Formula (12) 392 General CN General OH General H H H H Formula (12)Formula (12) Formula (12) 393 General CN General OH General H H CH₃ HFormula (12) Formula (12) Formula (12) 394 General CN General OH GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 395 General CN GeneralOH General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 396General CN General OH General H H Cl H Formula (12) Formula (12) Formula(12) 397 General CN General OH General H H F H Formula (12) Formula (12)Formula (12) 398 General CN OH General General H H H H Formula (12)Formula (12) Formula (12) 399 General CN OH General General H H CH₃ HFormula (12) Formula (12) Formula (12) 400 General CN OH General GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 401 OH CN GeneralGeneral General H H H H Formula (12) Formula (12) Formula (12) 402 OH CNGeneral General General H H CH₃ H Formula (12) Formula (12) Formula (12)403 OH CN General General General H H CH₃O H Formula (12) Formula (12)Formula (12) 404 General CN General OH OH H H H H Formula (12) Formula(12) 405 General CN General OH OH H H CH₃ H Formula (12) Formula (12)406 General CN General OH OH H H CH₃O H Formula (12) Formula (12) 407General CN OH General OH H H H H Formula (12) Formula (12) 408 GeneralCN OH General OH H H CH₃ H Formula (12) Formula (12) 409 General CN OHGeneral OH H H CH₃O H Formula (12) Formula (12) 410 OH CN GeneralGeneral OH H H H H Formula (12) Formula (12) 411 OH CN General GeneralOH H H CH₃ H Formula (12) Formula (12) 412 OH CN General General OH H HCH₃O H Formula (12) Formula (12) 413 General CN OH OH General H H H HFormula (12) Formula (12) 414 General CN OH OH General H H CH₃ H Formula(12) Formula (12) 415 General CN OH OH General H H CH₃O H Formula (12)Formula (12) 416 OH CN General OH General H H H H Formula (12) Formula(12) 417 OH CN General OH General H H CH₃ H Formula (12) Formula (12)418 OH CN General OH General H H CH₃O H Formula (12) Formula (12) 419 OHCN OH General General H H H H Formula (12) Formula (12) 420 OH CN OHGeneral General H H CH₃ H Formula (12) Formula (12) 421 OH CN OH GeneralGeneral H H CH₃O H Formula (12) Formula (12) 422 General CN OH OH OH H HH H Formula (12) 423 General CN OH OH OH H H CH₃ H Formula (12) 424General CN OH OH OH H H CH₃O H Formula (12) 425 OH CN General OH OH H HH H Formula (12) 426 OH CN General OH OH H H CH₃ H Formula (12) 427 OHCN General OH OH H H CH₃O H Formula (12) 428 OH CN OH General OH H H H HFormula (12) 429 OH CN OH General OH H H CH₃ H Formula (12) 430 OH CN OHGeneral OH H H CH₃O H Formula (12) 431 OH CN OH OH General H H H HFormula (12) 432 OH CN OH OH General H H CH₃ H Formula (12) 433 OH CN OHOH General H H CH₃O H Formula (12) 434 General CN General Cl General H HH H Formula (12) Formula (12) Formula (12) 435 General CN General ClGeneral H H CH₃ H Formula (12) Formula (12) Formula (12) 436 General CNGeneral Cl General H H CH₃O H Formula (12) Formula (12) Formula (12) 437General CN General Cl General H H t-C₄H₉ H Formula (12) Formula (12)Formula (12) 438 General CN General Cl General H H Cl H Formula (12)Formula (12) Formula (12) 439 General CN General Cl General H H F HFormula (12) Formula (12) Formula (12) 440 General CN General F GeneralH H H H Formula (12) Formula (12) Formula (12) 441 General CN General FGeneral H H CH₃ H Formula (12) Formula (12) Formula (12) 442 General CNGeneral F General H H CH₃O H Formula (12) Formula (12) Formula (12) 443General CN General F General H H t-C₄H₉ H Formula (12) Formula (12)Formula (12) 444 General CN General F General H H Cl H Formula (12)Formula (12) Formula (12) 445 General CN General F General H H F HFormula (12) Formula (12) Formula (12) 446 General CN General CH₃OGeneral H H H H Formula (12) Formula (12) Formula (12) 447 General CNGeneral CH₃O General H H CH₃ H Formula (12) Formula (12) Formula (12)448 General CN General CH₃O General H H CH₃O H Formula (12) Formula (12)Formula (12) 449 General CN General CH₃O General H H t-C₄H₉ H Formula(12) Formula (12) Formula (12) 450 General CN General CH₃O General H HCl H Formula (12) Formula (12) Formula (12) 451 General CN General CH₃OGeneral H H F H Formula (12) Formula (12) Formula (12) 452 General CNGeneral C₂H₅O General H H H H Formula (12) Formula (12) Formula (12) 453General CN General C₂H₅O General H H CH₃ H Formula (12) Formula (12)Formula (12) 454 General CN General C₂H₅O General H H CH₃O H Formula(12) Formula (12) Formula (12) 455 General CN General C₂H₅O General H Ht-C₄H₉ H Formula (12) Formula (12) Formula (12) 456 General CN GeneralC₂H₅O General H H Cl H Formula (12) Formula (12) Formula (12) 457General CN General C₂H₅O General H H F H Formula (12) Formula (12)Formula (12) 458 General CN General C₆H₅O General H H H H Formula (12)Formula (12) Formula (12) 459 General CN General C₆H₅O General H H CH₃ HFormula (12) Formula (12) Formula (12) 460 General CN General C₆H₅OGeneral H H CH₃O H Formula (12) Formula (12) Formula (12) 461 General CNGeneral C₆H₅O General H H t-C₄H₉ H Formula (12) Formula (12) Formula(12) 462 General CN General C₆H₅O General H H Cl H Formula (12) Formula(12) Formula (12) 463 General CN General C₆H₅O General H H F H Formula(12) Formula (12) Formula (12) 464 General CN General Formula (21)General H H H H Formula (12) Formula (12) Formula (12) 465 General CNGeneral Formula (21) General H H CH₃ H Formula (12) Formula (12) Formula(12) 466 General CN General Formula (21) General H H CH₃O H Formula (12)Formula (12) Formula (12) 467 General CN General Formula (21) General HH t-C₄H₉ H Formula (12) Formula (12) Formula (12) 468 General CN GeneralFormula (21) General H H Cl H Formula (12) Formula (12) Formula (12) 469General CN General Formula (21) General H H F H Formula (12) Formula(12) Formula (12) 470 General CN General Formula (22) General H H H HFormula (12) Formula (12) Formula (12) 471 General CN General Formula(22) General H H CH₃ H Formula (12) Formula (12) Formula (12) 472General CN General Formula (22) General H H CH₃O H Formula (12) Formula(12) Formula (12) 473 General CN General Formula (22) General H H t-C₄H₉H Formula (12) Formula (12) Formula (12) 474 General CN General Formula(22) General H H Cl H Formula (12) Formula (12) Formula (12) 475 GeneralCN General Formula (22) General H H F H Formula (12) Formula (12)Formula (12) 476 General CN General Formula (23) General H H H H Formula(12) Formula (12) Formula (12) 477 General CN General Formula (23)General H H CH₃ H Formula (12) Formula (12) Formula (12) 478 General CNGeneral Formula (23) General H H CH₃O H Formula (12) Formula (12)Formula (12) 479 General CN General Formula (23) General H H t-C₄H₉ HFormula (12) Formula (12) Formula (12) 480 General CN General Formula(23) General H H Cl H Formula (12) Formula (12) Formula (12) 481 GeneralCN General Formula (23) General H H F H Formula (12) Formula (12)Formula (12) 482 General CN General Formula (24) General H H H H Formula(12) Formula (12) Formula (12) 483 General CN General Formula (24)General H H CH₃ H Formula (12) Formula (12) Formula (12) 484 General CNGeneral Formula (24) General H H CH₃O H Formula (12) Formula (12)Formula (12) 485 General CN General Formula (24) General H H t-C₄H₉ HFormula (12) Formula (12) Formula (12) 486 General CN General Formula(24) General H H Cl H Formula (12) Formula (12) Formula (12) 487 GeneralCN General Formula (24) General H H F H Formula (12) Formula (12)Formula (12) 488 General CN General General General H C₆H₅ H H Formula(12) Formula (12) Formula (12) Formula (12) 489 General CN GeneralGeneral General H H C₆H₅ H Formula (12) Formula (12) Formula (12)Formula (12) 490 General CN General General H H C₆H₅ H H Formula (12)Formula (12) Formula (12) 491 General CN General General H H H C₆H₅ HFormula (12) Formula (12) Formula (12) 492 General CN General H GeneralH C₆H₅ H H Formula (12) Formula (12) Formula (12) 493 General CN GeneralH General H H C₆H₅ H Formula (12) Formula (12) Formula (12) 494 GeneralCN H General General H C₆H₅ H H Formula (12) Formula (12) Formula (12)495 General CN H General General H H C₆H₅ H Formula (12) Formula (12)Formula (12) 496 H CN General General General H C₆H₅ H H Formula (12)Formula (12) Formula (12) 497 H CN General General General H H C₆H₅ HFormula (12) Formula (12) Formula (12) 498 General CN General H H H C₆H₅H H Formula (12) Formula (12) 499 General CN General H H H H C₆H₅ HFormula (12) Formula (12)   500-1 General CN H General H H C₆H₅ H HFormula (12) Formula (12)   500-2 General CN H General H H H C₆H₅ HFormula (12) Formula (12)   500-3 H CN General General H H C₆H₅ H HFormula (12) Formula (12)   500-4 H CN General General H H H C₆H₅ HFormula (12) Formula (12)   500-5 General CN H H General H C₆H₅ H HFormula (12) Formula (12)   500-6 General CN H H General H H C₆H₅ HFormula (12) Formula (12)   500-7 H CN General H General H C₆H₅ H HFormula (12) Formula (12)   500-8 H CN General H General H H C₆H₅ HFormula (12) Formula (12)   500-9 H CN H General General H C₆H₅ H HFormula (12) Formula (12)   500-10 H CN H General General H H C₆H₅ HFormula (12) Formula (12)   500-11 General CN H H H H C₆H₅ H H Formula(12)   500-12 General CN H H H H H C₆H₅ H Formula (12)   500-13 H CNGeneral H H H C₆H₅ H H Formula (12)   500-14 H CN General H H H H C₆H₅ HFormula (12)   500-15 H CN H General H H C₆H₅ H H Formula (12)   500-16H CN H General H H H C₆H₅ H Formula (12)   500-17 General CN GeneralGeneral F H H C₆H₅ H Formula (12) Formula (12) Formula (12)   500-18General CN General F General H H C₆H₅ H Formula (12) Formula (12)Formula (12)   500-19 General CN F General General H H C₆H₅ H Formula(12) Formula (12) Formula (12)   500-20 F CN General General General H HC₆H₅ H Formula (12) Formula (12) Formula (12)   500-21 General CNGeneral F F H H C₆H₅ H Formula (12) Formula (12)   500-22 General CN FGeneral F H H C₆H₅ H Formula (12) Formula (12)   500-23 F CN GeneralGeneral F H H C₆H₅ H Formula (12) Formula (12)   500-24 General CN F FGeneral H H C₆H₅ H Formula (12) Formula (12)   500-25 F CN General FGeneral H H C₆H₅ H Formula (12) Formula (12)   500-26 F CN F GeneralGeneral H H C₆H₅ H Formula (12) Formula (12)   500-27 General CN F F F HH C₆H₅ H Formula (12)   500-28 F CN General F F H H C₆H₅ H Formula (12)  500-29 F CN F General F H H C₆H₅ H Formula (12)   500-30 General CNGeneral General OH H H C₆H₅ H Formula (12) Formula (12) Formula (12)  500-31 General CN General OH General H H C₆H₅ H Formula (12) Formula(12) Formula (12)   500-32 General CN OH General General H H C₆H₅ HFormula (12) Formula (12) Formula (12)   500-33 OH CN General GeneralGeneral H H C₆H₅ H Formula (12) Formula (12) Formula (12)   500-34General CN General OH OH H H C₆H₅ H Formula (12) Formula (12)   500-35General CN OH General OH H H C₆H₅ H Formula (12) Formula (12)   500-36OH CN General General OH H H C₆H₅ H Formula (12) Formula (12)   500-37General CN OH OH General H H C₆H₅ H Formula (12) Formula (12)   500-38OH CN General OH General H H C₆H₅ H Formula (12) Formula (12)   500-39OH CN OH General General H H C₆H₅ H Formula (12) Formula (12)   500-40General CN OH OH OH H H C₆H₅ H Formula (12)   500-41 OH CN General OH OHH H C₆H₅ H Formula (12)   500-42 OH CN OH General OH H H C₆H₅ H Formula(12)   500-43 OH CN OH OH General H H C₆H₅ H Formula (12)   500-44General CN General Cl General H H C₆H₅ H Formula (12) Formula (12)Formula (12)   500-45 General CN General F General H H C₆H₅ H Formula(12) Formula (12) Formula (12)   500-46 General CN General CH₃O GeneralH H C₆H₅ H Formula (12) Formula (12) Formula (12)   500-47 General CNGeneral C₂H₅O General H H C₆H₅ H Formula (12) Formula (12) Formula (12)  500-48 General CN General C₆H₅O General H H C₆H₅ H Formula (12)Formula (12) Formula (12)   500-49 General CN General Formula (21)General H H C₆H₅ H Formula (12) Formula (12) Formula (12)   500-50General CN General Formula (22) General H H C₆H₅ H Formula (12) Formula(12) Formula (12)   500-51 General CN General Formula (23) General H HC₆H₅ H Formula (12) Formula (12) Formula (12)   500-52 General CNGeneral Formula (24) General H H C₆H₅ H Formula (12) Formula (12)Formula (12)

TABLE 3 Compound General Formula (1) General Formula (12) No. R¹ R² R³R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 501 CN General General GeneralGeneral H H H H Formula (12) Formula (12) Formula (12) Formula (12) 502CN General General General General H CH₃ H H Formula (12) Formula (12)Formula (12) Formula (12) 503 CN General General General General H CH₃OH H Formula (12) Formula (12) Formula (12) Formula (12) 504 CN GeneralGeneral General General H H CH₃ H Formula (12) Formula (12) Formula (12)Formula (12) 505 CN General General General General H H CH₃O H Formula(12) Formula (12) Formula (12) Formula (12) 506 CN General GeneralGeneral General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12)Formula (12) 507 CN General General General General H H Cl H Formula(12) Formula (12) Formula (12) Formula (12) 508 CN General GeneralGeneral General H H F H Formula (12) Formula (12) Formula (12) Formula(12) 509 CN General General General General H H H CH₃ Formula (12)Formula (12) Formula (12) Formula (12) 510 CN General General GeneralGeneral H H H CH₃O Formula (12) Formula (12) Formula (12) Formula (12)511 CN General General General H H H H H Formula (12) Formula (12)Formula (12) 512 CN General General General H H H CH₃ H Formula (12)Formula (12) Formula (12) 513 CN General General General H H H CH₃O HFormula (12) Formula (12) Formula (12) 514 CN General General H GeneralH H H H Formula (12) Formula (12) Formula (12) 515 CN General General HGeneral H H CH₃ H Formula (12) Formula (12) Formula (12) 516 CN GeneralGeneral H General H H CH₃O H Formula (12) Formula (12) Formula (12) 517CN General General H H H H H H Formula (12) Formula (12) 518 CN GeneralGeneral H H H H CH₃ H Formula (12) Formula (12) 519 CN General General HH H H CH₃O H Formula (12) Formula (12) 520 CN General H General H H H HH Formula (12) Formula (12) 521 CN General H General H H H CH₃ H Formula(12) Formula (12) 522 CN General H General H H H CH₃O H Formula (12)Formula (12) 523 CN H General General H H H H H Formula (12) Formula(12) 524 CN H General General H H H CH₃ H Formula (12) Formula (12) 525CN H General General H H H CH₃O H Formula (12) Formula (12) 526 CNGeneral H H General H H H H Formula (12) Formula (12) 527 CN General H HGeneral H H CH₃ H Formula (12) Formula (12) 528 CN General H H General HH CH₃O H Formula (12) Formula (12) 529 CN General H H H H H H H Formula(12) 530 CN General H H H H H CH₃ H Formula (12) 531 CN General H H H HH CH₃O H Formula (12) 532 CN H General H H H H H H Formula (12) 533 CN HGeneral H H H H CH₃ H Formula (12) 534 CN H General H H H H CH₃O HFormula (12) 535 CN General General General F H H H H Formula (12)Formula (12) Formula (12) 536 CN General General General F H H CH₃ HFormula (12) Formula (12) Formula (12) 537 CN General General General FH H CH₃O H Formula (12) Formula (12) Formula (12) 538 CN General GeneralF General H H H H Formula (12) Formula (12) Formula (12) 539 CN GeneralGeneral F General H H CH₃ H Formula (12) Formula (12) Formula (12) 540CN General General F General H H CH₃O H Formula (12) Formula (12)Formula (12) 541 CN General General F F H H H H Formula (12) Formula(12) 542 CN General General F F H H CH₃ H Formula (12) Formula (12) 543CN General General F F H H CH₃O H Formula (12) Formula (12) 544 CNGeneral F General F H H H H Formula (12) Formula (12) 545 CN General FGeneral F H H CH₃ H Formula (12) Formula (12) 546 CN General F General FH H CH₃O H Formula (12) Formula (12) 547 CN F General General F H H H HFormula (12) Formula (12) 548 CN F General General F H H CH₃ H Formula(12) Formula (12) 549 CN F General General F H H CH₃O H Formula (12)Formula (12) 550 CN General F F General H H H H Formula (12) Formula(12) 551 CN General F F General H H CH₃ H Formula (12) Formula (12) 552CN General F F General H H CH₃O H Formula (12) Formula (12) 553 CNGeneral F F F H H H H Formula (12) 554 CN General F F F H H CH₃ HFormula (12) 555 CN General F F F H H CH₃O H Formula (12) 556 CN FGeneral F F H H H H Formula (12) 557 CN F General F F H H CH₃ H Formula(12) 558 CN F General F F H H CH₃O H Formula (12) 559 CN General GeneralGeneral OH H H H H Formula (12) Formula (12) Formula (12) 560 CN GeneralGeneral General OH H H CH₃ H Formula (12) Formula (12) Formula (12) 561CN General General General OH H H CH₃O H Formula (12) Formula (12)Formula (12) 562 CN General General OH General H H H H Formula (12)Formula (12) Formula (12) 563 CN General General OH General H H CH₃ HFormula (12) Formula (12) Formula (12) 654 CN General General OH GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 565 CN General GeneralOH General H H Cl H Formula (12) Formula (12) Formula (12) 566 CNGeneral General OH General H H F H Formula (12) Formula (12) Formula(12) 567 CN General General OH OH H H H H Formula (12) Formula (12) 568CN General General OH OH H H CH₃ H Formula (12) Formula (12) 569 CNGeneral General OH OH H H CH₃O H Formula (12) Formula (12) 570 CNGeneral OH General OH H H H H Formula (12) Formula (12) 571 CN GeneralOH General OH H H CH₃ H Formula (12) Formula (12) 572 CN General OHGeneral OH H H CH₃O H Formula (12) Formula (12) 573 CN OH GeneralGeneral OH H H H H Formula (12) Formula (12) 574 CN OH General GeneralOH H H CH₃ H Formula (12) Formula (12) 575 CN OH General General OH H HCH₃O H Formula (12) Formula (12) 576 CN General OH OH General H H H HFormula (12) Formula (12) 577 CN General OH OH General H H CH₃ H Formula(12) Formula (12) 578 CN General OH OH General H H CH₃O H Formula (12)Formula (12) 579 CN General OH OH OH H H H H Formula (12) 580 CN GeneralOH OH OH H H CH₃ H Formula (12) 581 CN General OH OH OH H H CH₃O HFormula (12) 582 CN OH General OH OH H H H H Formula (12) 583 CN OHGeneral OH OH H H CH₃ H Formula (12) 584 CN OH General OH OH H H CH₃O HFormula (12) 585 CN General General Cl General H H H H Formula (12)Formula (12) Formula (12) 586 CN General General Cl General H H CH₃ HFormula (12) Formula (12) Formula (12) 587 CN General General Cl GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 588 CN General GeneralCl General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 589 CNGeneral General Cl General H H Cl H Formula (12) Formula (12) Formula(12) 590 CN General General Cl General H H F H Formula (12) Formula (12)Formula (12) 591 CN General General F General H H H H Formula (12)Formula (12) Formula (12) 592 CN General General F General H H CH₃ HFormula (12) Formula (12) Formula (12) 593 CN General General F GeneralH H CH₃O H Formula (12) Formula (12) Formula (12) 594 CN General GeneralF General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12) 595 CNGeneral General F General H H Cl H Formula (12) Formula (12) Formula(12) 596 CN General General F General H H F H Formula (12) Formula (12)Formula (12) 597 CN General General CH₃O General H H H H Formula (12)Formula (12) Formula (12) 598 CN General General CH₃O General H H CH₃ HFormula (12) Formula (12) Formula (12) 599 CN General General CH₃OGeneral H H CH₃O H Formula (12) Formula (12) Formula (12) 600 CN GeneralGeneral CH₃O General H H t-C₄H₉ H Formula (12) Formula (12) Formula (12)601 CN General General CH₃O General H H Cl H Formula (12) Formula (12)Formula (12) 602 CN General General CH₃O General H H F H Formula (12)Formula (12) Formula (12) 603 CN General General C₂H₅O General H H H HFormula (12) Formula (12) Formula (12) 604 CN General General C₂H₅OGeneral H H CH₃ H Formula (12) Formula (12) Formula (12) 605 CN GeneralGeneral C₂H₅O General H H CH₃O H Formula (12) Formula (12) Formula (12)606 CN General General C₂H₅O General H H t-C₄H₉ H Formula (12) Formula(12) Formula (12) 607 CN General General C₂H₅O General H H Cl H Formula(12) Formula (12) Formula (12) 608 CN General General C₂H₅O General H HF H Formula (12) Formula (12) Formula (12) 609 CN General General C₆H₅OGeneral H H H H Formula (12) Formula (12) Formula (12) 610 CN GeneralGeneral C₆H₅O General H H CH₃ H Formula (12) Formula (12) Formula (12)611 CN General General C₆H₅O General H H CH₃O H Formula (12) Formula(12) Formula (12) 612 CN General General C₆H₅O General H H t-C₄H₉ HFormula (12) Formula (12) Formula (12) 613 CN General General C₆H₅OGeneral H H Cl H Formula (12) Formula (12) Formula (12) 614 CN GeneralGeneral C₆H₅O General H H F H Formula (12) Formula (12) Formula (12) 615CN General General Formula (21) General H H H H Formula (12) Formula(12) Formula (12) 616 CN General General Formula (21) General H H CH₃ HFormula (12) Formula (12) Formula (12) 617 CN General General Formula(21) General H H CH₃O H Formula (12) Formula (12) Formula (12) 618 CNGeneral General Formula (21) General H H t-C₄H₉ H Formula (12) Formula(12) Formula (12) 619 CN General General Formula (21) General H H Cl HFormula (12) Formula (12) Formula (12) 620 CN General General Formula(21) General H H F H Formula (12) Formula (12) Formula (12) 621 CNGeneral General Formula (22) General H H H H Formula (12) Formula (12)Formula (12) 622 CN General General Formula (22) General H H CH₃ HFormula (12) Formula (12) Formula (12) 623 CN General General Formula(22) General H H CH₃O H Formula (12) Formula (12) Formula (12) 624 CNGeneral General Formula (22) General H H t-C₄H₉ H Formula (12) Formula(12) Formula (12) 625 CN General General Formula (22) General H H Cl HFormula (12) Formula (12) Formula (12) 626 CN General General Formula(22) General H H F H Formula (12) Formula (12) Formula (12) 627 CNGeneral General Formula (23) General H H H H Formula (12) Formula (12)Formula (12) 628 CN General General Formula (23) General H H CH₃ HFormula (12) Formula (12) Formula (12) 629 CN General General Formula(23) General H H CH₃O H Formula (12) Formula (12) Formula (12) 630 CNGeneral General Formula (23) General H H t-C₄H₉ H Formula (12) Formula(12) Formula (12) 631 CN General General Formula (23) General H H Cl HFormula (12) Formula (12) Formula (12) 632 CN General General Formula(23) General H H F H Formula (12) Formula (12) Formula (12) 633 CNGeneral General Formula (24) General H H H H Formula (12) Formula (12)Formula (12) 634 CN General General Formula (24) General H H CH₃ HFormula (12) Formula (12) Formula (12) 635 CN General General Formula(24) General H H CH₃O H Formula (12) Formula (12) Formula (12) 636 CNGeneral General Formula (24) General H H t-C₄H₉ H Formula (12) Formula(12) Formula (12) 637 CN General General Formula (24) General H H Cl HFormula (12) Formula (12) Formula (12) 638 CN General General Formula(24) General H H F H Formula (12) Formula (12) Formula (12) 639 CNGeneral General General General H C₆H₅ H H Formula (12) Formula (12)Formula (12) Formula (12) 640 CN General General General General H HC₆H₅ H Formula (12) Formula (12) Formula (12) Formula (12) 641 CNGeneral General General H H C₆H₅ H H Formula (12) Formula (12) Formula(12) 642 CN General General General H H H C₆H₅ H Formula (12) Formula(12) Formula (12) 643 CN General General H General H C₆H₅ H H Formula(12) Formula (12) Formula (12) 644 CN General General H General H H C₆H₅H Formula (12) Formula (12) Formula (12) 645 CN General General H H HC₆H₅ H H Formula (12) Formula (12) 646 CN General General H H H H C₆H₅ HFormula (12) Formula (12) 647 CN General H General H H C₆H₅ H H Formula(12) Formula (12) 648 CN General H General H H H C₆H₅ H Formula (12)Formula (12) 649 CN H General General H H C₆H₅ H H Formula (12) Formula(12) 650 CN H General General H H H C₆H₅ H Formula (12) Formula (12) 651CN H H General General H C₆H₅ H H Formula (12) Formula (12) 652 CN H HGeneral General H H C₆H₅ H Formula (12) Formula (12) 653 CN General H HH H C₆H₅ H H Formula (12) 654 CN General H H H H H C₆H₅ H Formula (12)655 CN H General H H H C₆H₅ H H Formula (12) 656 CN H General H H H HC₆H₅ H Formula (12) 657 CN General General General F H H C₆H₅ H Formula(12) Formula (12) Formula (12) 658 CN General General F General H H C₆H₅H Formula (12) Formula (12) Formula (12) 659 CN General General F F H HC₆H₅ H Formula (12) Formula (12) 660 CN General F General F H H C₆H₅ HFormula (12) Formula (12) 661 CN F General General F H H C₆H₅ H Formula(12) Formula (12) 662 CN F F General General H H C₆H₅ H Formula (12)Formula (12) 663 CN General F F F H H C₆H₅ H Formula (12) 664 CN FGeneral F F H H C₆H₅ H Formula (12) 665 CN General General General OH HH C₆H₅ H Formula (12) Formula (12) Formula (12) 666 CN General GeneralOH General H H C₆H₅ H Formula (12) Formula (12) Formula (12) 667 CNGeneral General OH OH H H C₆H₅ H Formula (12) Formula (12) 668 CNGeneral OH General OH H H C₆H₅ H Formula (12) Formula (12) 669 CN OHGeneral General OH H H C₆H₅ H Formula (12) Formula (12) 670 CN OH OHGeneral General H H C₆H₅ H Formula (12) Formula (12) 671 CN General OHOH OH H H C₆H₅ H Formula (12) 672 CN OH General OH OH H H C₆H₅ H Formula(12) 673 CN General General Cl General H H C₆H₅ H Formula (12) Formula(12) Formula (12) 674 CN General General F General H H C₆H₅ H Formula(12) Formula (12) Formula (12) 675 CN General General CH₃O General H HC₆H₅ H Formula (12) Formula (12) Formula (12) 676 CN General GeneralC₂H₅O General H H C₆H₅ H Formula (12) Formula (12) Formula (12) 677 CNGeneral General C₆H₅O General H H C₆H₅ H Formula (12) Formula (12)Formula (12) 678 CN General General Formula (21) General H H C₆H₅ HFormula (12) Formula (12) Formula (12) 679 CN General General Formula(22) General H H C₆H₅ H Formula (12) Formula (12) Formula (12) 680 CNGeneral General Formula (23) General H H C₆H₅ H Formula (12) Formula(12) Formula (12) 681 CN General General Formula (24) General H H C₆H₅ HFormula (12) Formula (12) Formula (12)

TABLE 4 Compound General Formula (1) General Formula (13) No. R¹ R² R³R⁴ R⁵ R⁴¹ R⁴² R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 701 General General CN General General H HH H H H Formula Formula Formula Formula (13) (13) (13) (13) 702 GeneralGeneral CN General General H CH₃ H H H H Formula Formula Formula Formula(13) (13) (13) (13) 703 General General CN General General H CH₃O H H HH Formula Formula Formula Formula (13) (13) (13) (13) 704 GeneralGeneral CN General General H H CH₃ H H H Formula Formula Formula Formula(13) (13) (13) (13) 705 General General CN General General H H CH₃O H HH Formula Formula Formula Formula (13) (13) (13) (13) 706 GeneralGeneral CN General General H H t-C₄H₉ H H H Formula Formula FormulaFormula (13) (13) (13) (13) 707 General General CN General General H HCl H H H Formula Formula Formula Formula (13) (13) (13) (13) 708 GeneralGeneral CN General General H H F H H H Formula Formula Formula Formula(13) (13) (13) (13) 709 General General CN General General H H H CH₃ H HFormula Formula Formula Formula (13) (13) (13) (13) 710 General GeneralCN General General H H H CH₃O H H Formula Formula Formula Formula (13)(13) (13) (13) 711 General General CN General General H H H H CH₃ HFormula Formula Formula Formula (13) (13) (13) (13) 712 General GeneralCN General General H H H H CH₃O H Formula Formula Formula Formula (13)(13) (13) (13) 713 General General CN General General H H H H t-C₄H₉ HFormula Formula Formula Formula (13) (13) (13) (13) 714 General GeneralCN General General H H H H Cl H Formula Formula Formula Formula (13)(13) (13) (13) 715 General General CN General General H H H H F HFormula Formula Formula Formula (13) (13) (13) (13) 716 General GeneralCN General General H H H H C₆H₅ H Formula Formula Formula Formula (13)(13) (13) (13) 717 General General CN General General H H H H p-CH₃C₆H₄H Formula Formula Formula Formula (13) (13) (13) (13) 718 GeneralGeneral CN General General H H H H 2,4,6-(CH₃)₃C₆H₂ H Formula FormulaFormula Formula (13) (13) (13) (13) 719 General General CN GeneralGeneral H H H H p-CH₃OC₆H₄ H Formula Formula Formula Formula (13) (13)(13) (13) 720 General General CN General General H H H H p-(CH₃)₂NC₆H₂ HFormula Formula Formula Formula (13) (13) (13) (13) 721 General GeneralCN General General H H H H p-FC₆H₄ H Formula Formula Formula Formula(13) (13) (13) (13) 722 General General CN General General H H H Hp-CNC₆H₄ H Formula Formula Formula Formula (13) (13) (13) (13) 723General General CN General General H H H H H CH₃ Formula Formula FormulaFormula (13) (13) (13) (13) 724 General General CN General General H H HH H CH₃O Formula Formula Formula Formula (13) (13) (13) (13) 725 GeneralGeneral CN General General H H H H H t-C₄H₉ Formula Formula FormulaFormula (13) (13) (13) (13) 726 General General CN General General H H HH H Cl Formula Formula Formula Formula (13) (13) (13) (13) 727 GeneralGeneral CN General General H H H H H F Formula Formula Formula Formula(13) (13) (13) (13) 728 General General CN General General H H H H HC₆H₅ Formula Formula Formula Formula (13) (13) (13) (13) 729 GeneralGeneral CN General General H H H H H p-CH₃C₆H₄ Formula Formula FormulaFormula (13) (13) (13) (13) 730 General General CN General General H H HH H 2,4,6-(CH₃)₃C₆H₂ Formula Formula Formula Formula (13) (13) (13) (13)731 General General CN General General H H H H H p-CH₃OC₆H₄ FormulaFormula Formula Formula (13) (13) (13) (13) 732 General General CNGeneral General H H H H H p-(CH₃)₂NC₆H₄ Formula Formula Formula Formula(13) (13) (13) (13) 733 General General CN General General H H H H Hp-FC₆H₄ Formula Formula Formula Formula (13) (13) (13) (13) 734 GeneralGeneral CN General General H H H H H p-CNC₆H₄ Formula Formula FormulaFormula (13) (13) (13) (13) 735 General General CN General H H H H H H HFormula Formula Formula (13) (13) (13) 736 General General CN H GeneralH H H H H H Formula Formula Formula (13) (13) (13) 737 General GeneralCN H H H H H H H H Formula Formula (13) (13) 738 General H CN General HH H H H H H Formula Formula (13) (13) 739 H General CN General H H H H HH H Formula Formula (13) (13) 740 General H CN H H H H H H H H Formula(13) 741 General General CN General F H H H H H H Formula FormulaFormula (13) (13) (13) 742 General General CN F General H H H H H HFormula Formula Formula (13) (13) (13) 743 General General CN F F H H HH H H Formula Formula (13) (13) 744 General F CN General F H H H H H HFormula Formula (13) (13) 745 F General CN General F H H H H H H FormulaFormula (13) (13) 746 General F CN F F H H H H H H Formula (13) 747General General CN General OH H H H H H H Formula Formula Formula (13)(13) (13) 748 General General CN OH General H H H H H H Formula FormulaFormula (13) (13) (13) 749 General General CN OH OH H H H H H H FormulaFormula (13) (13) 750 General OH CN General OH H H H H H H FormulaFormula (13) (13) 751 OH General CN General OH H H H H H H FormulaFormula (13) (13) 752 General OH CN OH OH H H H H H H Formula (13) 753General General CN Cl General H H H H H H Formula Formula Formula (13)(13) (13) 754 General General CN Cl General H H CH₃ H H H FormulaFormula Formula (13) (13) (13) 755 General General CN Cl General H HCH₃O H H H Formula Formula Formula (13) (13) (13) 756 General General CNCl General H H t-C₄H₉ H H H Formula Formula Formula (13) (13) (13) 757General General CN Cl General H H Cl H H H Formula Formula Formula (13)(13) (13) 758 General General CN Cl General H H F H H H Formula FormulaFormula (13) (13) (13) 759 General General CN F General H H H H H HFormula Formula Formula (13) (13) (13) 760 General General CN F GeneralH H CH₃ H H H Formula Formula Formula (13) (13) (13) 761 General GeneralCN F General H H CH₃O H H H Formula Formula Formula (13) (13) (13) 762General General CN F General H H t-C₄H₉ H H H Formula Formula Formula(13) (13) (13) 763 General General CN F General H H Cl H H H FormulaFormula Formula (13) (13) (13) 764 General General CN F General H H F HH H Formula Formula Formula (13) (13) (13) 765 General General CN CH₃OGeneral H H H H H H Formula Formula Formula (13) (13) (13) 766 GeneralGeneral CN CH₃O General H H CH₃ H H H Formula Formula Formula (13) (13)(13) 767 General General CN CH₃O General H H CH₃O H H H Formula FormulaFormula (13) (13) (13) 768 General General CN CH₃O General H H t-C₄H₉ HH H Formula Formula Formula (13) (13) (13) 769 General General CN CH₃OGeneral H H Cl H H H Formula Formula Formula (13) (13) (13) 770 GeneralGeneral CN CH₃O General H H F H H H Formula Formula Formula (13) (13)(13) 771 General General CN C₂H₅O General H H H H H H Formula FormulaFormula (13) (13) (13) 772 General General CN C₂H₅O General H H CH₃ H HH Formula Formula Formula (13) (13) (13) 773 General General CN C₂H₅OGeneral H H CH₃O H H H Formula Formula Formula (13) (13) (13) 774General General CN C₂H₅O General H H t-C₄H₉ H H H Formula FormulaFormula (13) (13) (13) 775 General General CN C₂H₅O General H H Cl H H HFormula Formula Formula (13) (13) (13) 776 General General CN C₂H₅OGeneral H H F H H H Formula Formula Formula (13) (13) (13) 777 GeneralGeneral CN C₆H₅O General H H H H H H Formula Formula Formula (13) (13)(13) 778 General General CN C₆H₅O General H H CH₃ H H H Formula FormulaFormula (13) (13) (13) 779 General General CN C₆H₅O General H H CH₃O H HH Formula Formula Formula (13) (13) (13) 780 General General CN C₆H₅OGeneral H H t-C₄H₉ H H H Formula Formula Formula (13) (13) (13) 781General General CN C₆H₅O General H H Cl H H H Formula Formula Formula(13) (13) (13) 782 General General CN C₆H₅O General H H F H H H FormulaFormula Formula (13) (13) (13) 783 General General CN Formula General HH H H H H Formula Formula (21) Formula (13) (13) (13) 784 GeneralGeneral CN Formula General H H CH₃ H H H Formula Formula (21) Formula(13) (13) (13) 785 General General CN Formula General H H CH₃O H H HFormula Formula (21) Formula (13) (13) (13) 786 General General CNFormula General H H t-C₄H₉ H H H Formula Formula (21) Formula (13) (13)(13) 787 General General CN Formula General H H Cl H H H Formula Formula(21) Formula (13) (13) (13) 788 General General CN Formula General H H FH H H Formula Formula (21) Formula (13) (13) (13) 789 General General CNFormula General H H H H H H Formula Formula (22) Formula (13) (13) (13)790 General General CN Formula General H H CH₃ H H H Formula Formula(22) Formula (13) (13) (13) 791 General General CN Formula General H HCH₃O H H H Formula Formula (22) Formula (13) (13) (13) 792 GeneralGeneral CN Formula General H H t-C₄H₉ H H H Formula Formula (22) Formula(13) (13) (13) 793 General General CN Formula General H H Cl H H HFormula Formula (22) Formula (13) (13) (13) 794 General General CNFormula General H H F H H H Formula Formula (22) Formula (13) (13) (13)795 General General CN Formula General H H H H H H Formula Formula (23)Formula (13) (13) (13) 796 General General CN Formula General H H CH₃ HH H Formula Formula (23) Formula (13) (13) (13) 797 General General CNFormula General H H CH₃O H H H Formula Formula (23) Formula (13) (13)(13) 798 General General CN Formula General H H t-C₄H₉ H H H FormulaFormula (23) Formula (13) (13) (13) 799 General General CN FormulaGeneral H H Cl H H H Formula Formula (23) Formula (13) (13) (13) 800General General CN Formula General H H F H H H Formula Formula (23)Formula (13) (13) (13) 801 General General CN Formula General H H H H HH Formula Formula (24) Formula (13) (13) (13) 802 General General CNFormula General H H CH₃ H H H Formula Formula (24) Formula (13) (13)(13) 803 General General CN Formula General H H CH₃O H H H FormulaFormula (24) Formula (13) (13) (13) 804 General General CN FormulaGeneral H H t-C₄H₉ H H H Formula Formula (24) Formula (13) (13) (13) 805General General CN Formula General H H Cl H H H Formula Formula (24)Formula (13) (13) (13) 806 General General CN Formula General H H F H HH Formula Formula (24) Formula (13) (13) (13)

TABLE 5 General Formula (14) Com- R⁵², pound General Formula (1) R⁵⁶,R⁵⁸, No. R¹ R² R³ R⁴ R⁵ R⁵² R⁵³ R⁵⁴ R⁵⁵ R⁵⁷ R⁵⁹ R⁶¹ R⁶⁰, R⁶² 901 GeneralGeneral CN General General H H H H H H H H Formula (14) Formula (14)Formula (14) Formula (14) 902 General General CN General General CH₃ H HH H H H H Formula (14) Formula (14) Formula (14) Formula (14) 903General General CN General General CH₃O H H H H H H H Formula (14)Formula (14) Formula (14) Formula (14) 904 General General CN GeneralGeneral H CH₃ H H H H H H Formula (14) Formula (14) Formula (14) Formula(14) 905 General General CN General General H CH₃O H H H H H H Formula(14) Formula (14) Formula (14) Formula (14) 906 General General CNGeneral General H t-C₄H₉ H H H H H H Formula (14) Formula (14) Formula(14) Formula (14) 907 General General CN General General H Cl H H H H HH Formula (14) Formula (14) Formula (14) Formula (14) 908 GeneralGeneral CN General General H F H H H H H H Formula (14) Formula (14)Formula (14) Formula (14) 909 General General CN General General H H CH₃H H H H H Formula (14) Formula (14) Formula (14) Formula (14) 910General General CN General General H H CH₃O H H H H H Formula (14)Formula (14) Formula (14) Formula (14) 911 General General CN GeneralGeneral H H H CH₃ H H H H Formula (14) Formula (14) Formula (14) Formula(14) 912 General General CN General General H H H CH₃O H H H H Formula(14) Formula (14) Formula (14) Formula (14) 913 General General CNGeneral General H H H H CH₃ H H H Formula (14) Formula (14) Formula (14)Formula (14) 914 General General CN General General H H H H CH₃O H H HFormula (14) Formula (14) Formula (14) Formula (14) 915 General GeneralCN General General H H H H H CH₃ H H Formula (14) Formula (14) Formula(14) Formula (14) 916 General General CN General General H H H H H CH₃OH H Formula (14) Formula (14) Formula (14) Formula (14) 917 GeneralGeneral CN General General H H H H H H CH₃ H Formula (14) Formula (14)Formula (14) Formula (14) 918 General General CN General General H H H HH H CH₃O H Formula (14) Formula (14) Formula (14) Formula (14) 919General General CN General H H H H H H H H H Formula (14) Formula (14)Formula (14) 920 General General CN H General H H H H H H H H Formula(14) Formula (14) Formula (14) 921 General General CN H H H H H H H H HH Formula (14) Formula (14) 922 General H CN General H H H H H H H H HFormula (14) Formula (14) 923 H General CN General H H H H H H H H HFormula (14) Formula (14) 924 General H CN H H H H H H H H H H Formula(14) 925 General General CN General F H H H H H H H H Formula (14)Formula (14) Formula (14) 926 General General CN F General H H H H H H HH Formula (14) Formula (14) Formula (14) 927 General General CN F F H HH H H H H H Formula (14) Formula (14) 928 General F CN General F H H H HH H H H Formula (14) Formula (14) 929 F General CN General F H H H H H HH H Formula (14) Formula (14) 930 General F CN F F H H H H H H H HFormula (14) 931 General General CN General OH H H H H H H H H Formula(14) Formula (14) Formula (14) 932 General General CN OH General H H H HH H H H Formula (14) Formula (14) Formula (14) 933 General General CN OHOH H H H H H H H H Formula (14) Formula (14) 934 General OH CN GeneralOH H H H H H H H H Formula (14) Formula (14) 935 OH General CN GeneralOH H H H H H H H H Formula (14) Formula (14) 936 General OH CN OH OH H HH H H H H H Formula (14) 937 General General CN Cl General H H H H H H HH Formula (14) Formula (14) Formula (14) 938 General General CN ClGeneral H CH₃ H H H H H H Formula (14) Formula (14) Formula (14) 939General General CN Cl General H CH₃O H H H H H H Formula (14) Formula(14) Formula (14) 940 General General CN Cl General H t-C₄H₉ H H H H H HFormula (14) Formula (14) Formula (14) 941 General General CN Cl GeneralH Cl H H H H H H Formula (14) Formula (14) Formula (14) 942 GeneralGeneral CN Cl General H F H H H H H H Formula (14) Formula (14) Formula(14) 943 General General CN F General H H H H H H H H Formula (14)Formula (14) Formula (14) 944 General General CN F General H CH₃ H H H HH H Formula (14) Formula (14) Formula (14) 945 General General CN FGeneral H CH₃O H H H H H H Formula (14) Formula (14) Formula (14) 946General General CN F General H t-C₄H₉ H H H H H H Formula (14) Formula(14) Formula (14) 947 General General CN F General H Cl H H H H H HFormula (14) Formula (14) Formula (14) 948 General General CN F GeneralH F H H H H H H Formula (14) Formula (14) Formula (14) 949 GeneralGeneral CN CH₃O General H H H H H H H H Formula (14) Formula (14)Formula (14) 950 General General CN CH₃O General H CH₃ H H H H H HFormula (14) Formula (14) Formula (14) 951 General General CN CH₃OGeneral H CH₃O H H H H H H Formula (14) Formula (14) Formula (14) 952General General CN CH₃O General H t-C₄H₉ H H H H H H Formula (14)Formula (14) Formula (14) 953 General General CN CH₃O General H Cl H H HH H H Formula (14) Formula (14) Formula (14) 954 General General CN CH₃OGeneral H F H H H H H H Formula (14) Formula (14) Formula (14) 955General General CN C₂H₃O General H H H H H H H H Formula (14) Formula(14) Formula (14) 956 General General CN C₂H₃O General H CH₃ H H H H H HFormula (14) Formula (14) Formula (14) 957 General General CN C₂H₆OGeneral H CH₃O H H H H H H Formula (14) Formula (14) Formula (14) 958General General CN C₂H₆O General H t-C₄H₉ H H H H H H Formula (14)Formula (14) Formula (14) 959 General General CN C₂H₆O General H Cl H HH H H H Formula (14) Formula (14) Formula (14) 960 General General CNC₂H₆O General H F H H H H H H Formula (14) Formula (14) Formula (14) 961General General CN C₆H₅O General H H H H H H H H Formula (14) Formula(14) Formula (14) 962 General General CN C₆H₅O General H CH₃ H H H H H HFormula (14) Formula (14) Formula (14) 963 General General CN C₆H₅OGeneral H CH₃O H H H H H H Formula (14) Formula (14) Formula (14) 964General General CN C₆H₅O General H t-C₄H₉ H H H H H H Formula (14)Formula (14) Formula (14) 965 General General CN C₆H₅O General H Cl H HH H H H Formula (14) Formula (14) Formula (14) 966 General General CNC₆H₅O General H F H H H H H H Formula (14) Formula (14) Formula (14) 967General General CN Formula (21) General H H H H H H H H Formula (14)Formula (14) Formula (14) 968 General General CN Formula (21) General HCH₃ H H H H H H Formula (14) Formula (14) Formula (14) 969 GeneralGeneral CN Formula (21) General H CH₃O H H H H H H Formula (14) Formula(14) Formula (14) 970 General General CN Formula (21) General H t-C₄H₉ HH H H H H Formula (14) Formula (14) Formula (14) 971 General General CNFormula (21) General H Cl H H H H H H Formula (14) Formula (14) Formula(14) 972 General General CN Formula (21) General H F H H H H H H Formula(14) Formula (14) Formula (14) 973 General General CN Formula (22)General H H H H H H H H Formula (14) Formula (14) Formula (14) 974General General CN Formula (22) General H CH₃ H H H H H H Formula (14)Formula (14) Formula (14) 975 General General CN Formula (22) General HCH₃O H H H H H H Formula (14) Formula (14) Formula (14) 976 GeneralGeneral CN Formula (22) General H t-C₄H₉ H H H H H H Formula (14)Formula (14) Formula (14) 977 General General CN Formula (22) General HCl H H H H H H Formula (14) Formula (14) Formula (14) 978 GeneralGeneral CN Formula (22) General H F H H H H H H Formula (14) Formula(14) Formula (14) 989 General General CN Formula (23) General H H H H HH H H Formula (14) Formula (14) Formula (14) 980 General General CNFormula (23) General H CH₃ H H H H H H Formula (14) Formula (14) Formula(14) 981 General General CN Formula (23) General H CH₃O H H H H H HFormula (14) Formula (14) Formula (14) 982 General General CN Formula(23) General H t-C₄H₉ H H H H H H Formula (14) Formula (14) Formula (14)983 General General CN Formula (23) General H Cl H H H H H H Formula(14) Formula (14) Formula (14) 984 General General CN Formula (23)General H F H H H H H H Formula (14) Formula (14) Formula (14) 985General General CN Formula (24) General H H H H H H H H Formula (14)Formula (14) Formula (14) 986 General General CN Formula (24) General HCH₃ H H H H H H Formula (14) Formula (14) Formula (14) 987 GeneralGeneral CN Formula (24) General H CH₃O H H H H H H Formula (14) Formula(14) Formula (14) 988 General General CN Formula (24) General H t-C₄H₉ HH H H H H Formula (14) Formula (14) Formula (14) 989 General General CNFormula (24) General H Cl H H H H H H Formula (14) Formula (14) Formula(14) 990 General General CN Formula (24) General H F H H H H H H Formula(14) Formula (14) Formula (14)

TABLE 6 General Formula (15) Compound General Formula (1) R⁷⁵, No. R¹ R²R³ R⁴ R⁵ R⁷¹, R⁸⁰ R⁷², R⁷⁹ R⁷³, R⁷⁸ R⁷⁴, R⁷⁷ R⁷⁶ 1001 General General CNGeneral General H H H H H Formula (15) Formula (15) Formula (15) Formula(15) 1002 General General CN General General H CH₃ H H H Formula (15)Formula (15) Formula (15) Formula (15) 1003 General General CN GeneralGeneral H CH₃O H H H Formula (15) Formula (15) Formula (15) Formula (15)1004 General General CN General General H C₄H₉ H H H Formula (15)Formula (15) Formula (15) Formula (15) 1005 General General CN GeneralGeneral H CH₃ H CH₃ H Formula (15) Formula (15) Formula (15) Formula(15) 1006 General General CN General General H CH₃O H CH₃O H Formula(15) Formula (15) Formula (15) Formula (15) 1007 General General CNGeneral General H C₆H₅ H C₆H₅ H Formula (15) Formula (15) Formula (15)Formula (15) 1008 General General CN General General H H CH₃ H H Formula(15) Formula (15) Formula (15) Formula (15) 1009 General General CNGeneral General H H CH₃O H H Formula (15) Formula (15) Formula (15)Formula (15) 1010 General General CN General General H H t-C₄H₉ H HFormula (15) Formula (15) Formula (15) Formula (15) 1011 General GeneralCN General General H H Cl H H Formula (15) Formula (15) Formula (15)Formula (15) 1012 General General CN General General H H F H H Formula(15) Formula (15) Formula (15) Formula (15) 1013 General General CNGeneral General H H C₆H₅ H H Formula (15) Formula (15) Formula (15)Formula (15) 1014 General General CN General General H H p-C₆H₅—C₆H₄ H HFormula (15) Formula (15) Formula (15) Formula (15) 1015 General GeneralCN General H H H H H H Formula (15) Formula (15) Formula (15) 1016General General CN H General H H H H H Formula (15) Formula (15) Formula(15) 1017 General General CN H H H H H H H Formula (15) Formula (15)1018 General H CN General H H H H H H Formula (15) Formula (15) 1019 HGeneral CN General H H H H H H Formula (15) Formula (15) 1020 General HCN H H H H H H H Formula (15) 1021 General General CN General F H H H HH Formula (15) Formula (15) Formula (15) 1022 General General CN FGeneral H H H H H Formula (15) Formula (15) Formula (15) 1023 GeneralGeneral CN F F H H H H H Formula (15) Formula (15) 1024 General F CNGeneral F H H H H H Formula (15) Formula (15) 1025 F General CN GeneralF H H H H H Formula (15) Formula (15) 1026 General F CN F F H H H H HFormula (15) 1027 General General CN General OH H H H H H Formula (15)Formula (15) Formula (15) 1028 General General CN OH General H H H H HFormula (15) Formula (15) Formula (15) 1029 General General CN OH OH H HH H H Formula (15) Formula (15) 1030 General OH CN General OH H H H H HFormula (15) Formula (15) 1031 OH General CN General OH H H H H HFormula (15) Formula (15) 1032 General OH CN OH OH H H H H H Formula(15) 1033 General General CN Cl General H H H H H Formula (15) Formula(15) Formula (15) 1034 General General CN Cl General H H CH₃ H H Formula(15) Formula (15) Formula (15) 1035 General General CN Cl General H HCH₃O H H Formula (15) Formula (15) Formula (15) 1036 General General CNCl General H H t-C₄H₉ H H Formula (15) Formula (15) Formula (15) 1037General General CN Cl General H H Cl H H Formula (15) Formula (15)Formula (15) 1038 General General CN Cl General H H F H H Formula (15)Formula (15) Formula (15) 1039 General General CN F General H H H H HFormula (15) Formula (15) Formula (15) 1040 General General CN F GeneralH H CH₃ H H Formula (15) Formula (15) Formula (15) 1041 General GeneralCN F General H H CH₃O H H Formula (15) Formula (15) Formula (15) 1042General General CN F General H H t-C₄H₉ H H Formula (15) Formula (15)Formula (15) 1043 General General CN F General H H Cl H H Formula (15)Formula (15) Formula (15) 1044 General General CN F General H H F H HFormula (15) Formula (15) Formula (15) 1045 General General CN CH₃OGeneral H H H H H Formula (15) Formula (15) Formula (15) 1046 GeneralGeneral CN CH₃O General H H CH₃ H H Formula (15) Formula (15) Formula(15) 1047 General General CN CH₃O General H H CH₃O H H Formula (15)Formula (15) Formula (15) 1048 General General CN CH₃O General H Ht-C₄H₉ H H Formula (15) Formula (15) Formula (15) 1049 General GeneralCN CH₃O General H H Cl H H Formula (15) Formula (15) Formula (15) 1050General General CN CH₃O General H H F H H Formula (15) Formula (15)Formula (15) 1051 General General CN C₂H₅O General H H H H H Formula(15) Formula (15) Formula (15) 1052 General General CN C₂H₅O General H HCH₃ H H Formula (15) Formula (15) Formula (15) 1053 General General CNC₂H₅O General H H CH₃O H H Formula (15) Formula (15) Formula (15) 1054General General CN C₂H₅O General H H t-C₄H₉ H H Formula (15) Formula(15) Formula (15) 1055 General General CN C₂H₅O General H H Cl H HFormula (15) Formula (15) Formula (15) 1056 General General CN C₂H₅OGeneral H H F H H Formula (15) Formula (15) Formula (15) 1057 GeneralGeneral CN C₆H₅O General H H H H H Formula (15) Formula (15) Formula(15) 1058 General General CN C₆H₅O General H H CH₃ H H Formula (15)Formula (15) Formula (15) 1059 General General CN C₆H₅O General H H CH₃OH H Formula (15) Formula (15) Formula (15) 1060 General General CN C₆H₅OGeneral H H t-C₄H₉ H H Formula (15) Formula (15) Formula (15) 1061General General CN C₆H₅O General H H Cl H H Formula (15) Formula (15)Formula (15) 1062 General General CN C₆H₅O General H H F H H Formula(15) Formula (15) Formula (15) 1063 General General CN Formula (21)General H H H H H Formula (15) Formula (15) Formula (15) 1064 GeneralGeneral CN Formula (21) General H H CH₃ H H Formula (15) Formula (15)Formula (15) 1065 General General CN Formula (21) General H H CH₃O H HFormula (15) Formula (15) Formula (15) 1066 General General CN Formula(21) General H H t-C₄H₉ H H Formula (15) Formula (15) Formula (15) 1067General General CN Formula (21) General H H Cl H H Formula (15) Formula(15) Formula (15) 1068 General General CN Formula (21) General H H F H HFormula (15) Formula (15) Formula (15) 1069 General General CN Formula(22) General H H H H H Formula (15) Formula (15) Formula (15) 1070General General CN Formula (22) General H H CH₃ H H Formula (15) Formula(15) Formula (15) 1071 General General CN Formula (22) General H H CH₃OH H Formula (15) Formula (15) Formula (15) 1072 General General CNFormula (22) General H H t-C₄H₉ H H Formula (15) Formula (15) Formula(15) 1073 General General CN Formula (22) General H H Cl H H Formula(15) Formula (15) Formula (15) 1074 General General CN Formula (22)General H H F H H Formula (15) Formula (15) Formula (15) 1075 GeneralGeneral CN Formula (23) General H H H H H Formula (15) Formula (15)Formula (15) 1076 General General CN Formula (23) General H H CH₃ H HFormula (15) Formula (15) Formula (15) 1077 General General CN Formula(23) General H H CH₃O H H Formula (15) Formula (15) Formula (15) 1078General General CN Formula (23) General H H t-C₄H₉ H H Formula (15)Formula (15) Formula (15) 1079 General General CN Formula (23) General HH Cl H H Formula (15) Formula (15) Formula (15) 1080 General General CNFormula (23) General H H F H H Formula (15) Formula (15) Formula (15)1081 General General CN Formula (24) General H H H H H Formula (15)Formula (15) Formula (15) 1082 General General CN Formula (24) General HH CH₃ H H Formula (15) Formula (15) Formula (15) 1083 General General CNFormula (24) General H H CH₃O H H Formula (15) Formula (15) Formula (15)1084 General General CN Formula (24) General H H t-C₄H₉ H H Formula (15)Formula (15) Formula (15) 1085 General General CN Formula (24) General HH Cl H H Formula (15) Formula (15) Formula (15) 1086 General General CNFormula (24) General H H F H H Formula (15) Formula (15) Formula (15)

In the case where an organic layer containing the compound representedby the general formula (1) is to be produced by vapor deposition method,for example, one molecular weight of the compound represented by thegeneral formula (1) is preferably 1,500 or less, more preferably 1,200or less, further preferably 1,000 or less, and still further preferably800 or less. The lower limit of the molecular weight is generally 247 ormore, and preferably 290 or more.

The compound represented by the general formula (1) may be formed into afilm by a coating method irrespective of the molecular weight thereof. Afilm may be formed with the compound hawing a relatively large molecularweight by a coating method.

As an application of the invention, a compound that contains pluralstructures each represented by the general formula (1) in the moleculemay be used in a light-emitting layer of an organic light-emittingdevice.

For example, a polymer that is obtained by polymerizing a polymerizablemonomer having a structure represented by the general formula (1) may beused in a light-emitting layer of an organic light-emitting device.Specifically, a monomer having a polymerizable functional group in anyof R¹ to R⁵ in the general formula (1) may be prepared andhomopolymerized or copolymerized with another monomer to provide apolymer having the repeating unit, and the polymer may be used in alight-emitting layer of an organic light-emitting device. Alternatively,compounds each having a structure represented by the general formula (1)may be coupled to form a dimer or a trimer, and the dimer or the trimermay be used in a light-emitting layer of an organic light-emittingdevice.

Examples of the structure of the repeating unit constituting the polymercontaining the structure represented by the general formula (1) includeones having a structure, in which any of R¹ to R⁵ in the general formula(1) is represented by the following general formula (17) or (18).

In the general formulae (17) and (18), L¹ and L² represent a linkinggroup. The linking group preferably has from 0 to 20 carbon atoms, morepreferably from 1 to 15 carbon atoms, and further preferably from 2 to10 carbon atoms. The linking group preferably has a structurerepresented by -X¹¹-L¹¹-, wherein X¹¹ represents an oxygen atom or asulfur atom, and preferably an oxygen atom, and L¹¹ represents a linkinggroup, preferably a substituted or unsubstituted alkylene group or asubstituted or unsubstituted arylene group, and more preferably asubstituted or unsubstituted alkylene group having from 1 to 10 carbonatoms or a substituted or unsubstituted phenylene group.

In the general formulae (17) and (18), R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ eachindependently represent a substituent, preferably a substituted orunsubstituted alkyl group having from 1 to 6 carbon atoms, a substitutedof unsubstituted alkoxy group having from 1 to 6 carbon atoms, or ahalogen atom, more preferably an unsubstituted alkyl group having from 1to 3 carbon atoms, an unsubstituted alkoxy group having from 1 to 3carbon atoms, a fluorine atom, or a chlorine atom, and furtherpreferably an unsubstituted alkyl group having from 1 to 3 carbon atomsor an unsubstituted alkoxy group having from 1 to 3 carbon atoms.

Specific examples of the structure of the repeating unit include oneshaving a structure, in which any of R¹ to R⁵ in the general formula (1)is the following formulae (21) to (24). Two or more of R¹ to R⁵ may bethe formulae (21) to (24), and it is preferred that one of R¹ to R⁵ isthe formulae (21) to (24).

The polymer having the repeating unit containing the formulae (21) to(24) may be synthesized in such a manner that with at least one of R¹ toR⁵ in the general formula (1) that is a hydroxy group, the followingcompounds is reacted with the hydroxy group as a linker to introduce apolymerizable group thereto, and the polymerizable group is thenpolymerized.

The polymer containing the structure represented by the general formula(1) in the molecule may be a polymer that is formed only of a repeatingunit having the structure represented by the general formula (1), or maybe a polymer that further contains a repeating unit having anotherstructure. The repeating unit having the structure represented by thegeneral formula (1) contained in the polymer may be formed of a singlespecies or two or more species. Examples of the repeating unit that doesnot have the structure represented by the general formula (1) includeones derived from monomers that are ordinarily used in copolymerization.Examples thereof include a repeating unit derived from a monomer havingan ethylenic unsaturated bond, such as ethylene and styrene.

Compound Represented by General Formula (2)

In the compound represented by the general formula (1), a compoundhaving a structure represented by the following general formula (2) is anovel compound.

In the general formula (2), at least one of R¹¹, R¹², R¹⁴ and R¹⁵represents a cyano group, at least three of R¹¹ to R¹⁵ each represent asubstituted or unsubstituted 9-carbazolyl group, a substituted orunsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, a substituted orunsubstituted 1-indolyl group or a substituted or unsubstituteddiarylamino group, and the balance of R¹¹ to R¹⁵ represents a hydroxygroup.

In R¹¹ to R¹⁵ in the general formula (2), any one of R¹¹ and R¹² ispreferably a cyano group. At least three of R¹¹ to R¹⁵ each represent a9-carbazolyl group or the like, and these three substituents may be thesame as or different from each other, and it is preferred that all ofthem are the same as each other. At least three of R¹¹ to R¹⁵ eachpreferably represent a group having a structure represented by any ofthe general formulae (12) to (15). For specific examples and preferredranges of the general formulae (12) to (15), reference may be made tothe corresponding description for the general formula (1). In R¹¹ to R¹⁵in the general formula (2), none or one of them is a hydroxy group. Inthe case where one of them is a hydroxy group, the hydroxy group, ispreferably R¹⁴. Examples of the case include the case where R¹²represents a cyano group, and R¹⁴ represents a hydroxy group.

The synthesis method of the compound represented by the general formula(2) is not particularly limited. The compound represented by the generalformula (2) may be synthesized by combining known synthesis methods andconditions appropriately.

Preferred examples of the synthesis method include a method of preparingtetrafluorodicyanobenzene and then reacting the same with carbazole,indole, a diarylamine or the like. According to the reaction, such acompound may be synthesized that is represented by the general formula(2), wherein any one of R¹¹ to R¹⁵ represents a cyano group, and thebalance thereof each represents a carbazolyl group, an indolyl group ora diarylamino group. By using trifluorotricyanobenzene as the startingmaterial, such a compound may be synthesized that is represented by thegeneral formula (2), wherein any two of R¹³ to R¹⁵ each represent acyano group, and the balance thereof each represents a carbazolyl group,an indolyl group or a diarylamino group. Furthermore, a hydroxy groupmay be introduced to the benzene ring by performing, for example, aprocess of adding water and applying ultrasonic warns thereto.

For the details of the reaction, reference may be made to the synthesisexamples described later. The compound represented by the generalformula (2) may be synthesized by combining other known synthesisreactions.

Compound Represented by General Formula (3)

In the compound, represented by the general formula (1), a compoundhaving a structure represented by the following general formula (3) isuseful as a blue light-emitting material.

In the general formula (3), one of R⁸¹ to R⁸⁵ represents a cyano group,two of R⁸¹ to R⁸⁵ each represent a substituted or unsubstituted9-carbazolyl group, and the other two thereof each represent a hydrogenatom.

Specific examples of the compound represented by the general formula (3)will be shown below, but the compound represented by the general formula(3) capable of being used in the invention is not construed as beinglimited to the specific examples. In the following specific examples, Czrepresents a 9-carbazolyl group. Examples thereof also include compound,wherein Cz represents a 3-methylcarbazol-9-yl group or a3,6-dimethylcarbazol-9-yl group.

Organic Light-Emitting Device

The compound represented by the general formula (1) of the invention isuseful as a light-emitting material of an organic light-emitting device.The compound represented by the general formula (1) of the inventionthus may be effectively used as a light-emitting material in alight-emitting layer of an organic light-emitting device. The compoundrepresented by the general formula (1) includes a delayed fluorescentmaterial emitting delayed fluorescent light (i.e. delayed fluorescentemitter). Accordingly, the invention also relates to an invention of adelayed fluorescent emitter having a structure represented by thegeneral formula (1), an invention of the use of the compound representedby the general formula (1) as a delayed fluorescent emitter, and aninvention of a method of emitting delayed fluorescent light with thecompound represented by the general formula (1). An organiclight-emitting device using the compound as a light-emitting materialhas features that the device emits delayed fluorescent light and has ahigh light emission efficiency. The principle of the features will bedescribed as follows for an organic electroluminescent device as anexample.

In an organic electroluminescent device, carriers ere injected from ananode and a cathode to a light-emitting material to form an excitedstate for the light-emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescent device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy utilization. However, the excited triplet statehas a long lifetime and thus causes saturation of the excited state anddeactivation of energy through mutual action with the excitons in theexcited triplet state, and therefore the quantum efficiency ofphosphorescence may generally be often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescentdevice. In the case where a delayed fluorescent material is used in anorganic electroluminescent device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited single state hasthe same wavelength as fluorescent light since it is light emission fromthe excited single state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited single state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.

The use of the compound represented by the general formula (1) of theinvention as a light-emitting material of a light-emitting layer mayprovide an excellent organic light-emitting device, such as an organicphotoluminescent device (organic PL device) and an organicelectroluminescent device (organic EL device). The organicphotoluminescent device has a structure containing a substrate havingformed thereon at least a light-emitting layer. The organicelectroluminescent device has a structure containing at least an anode,a cathode and an organic layer formed between the anode and the cathode.The organic layer contains at least a light-emitting layer, and may beformed only of a light-emitting layer, or may have one or more organiclayer in addition, to the light-emitting layer. Examples of the organiclayer include a hole transporting layer, a hole injection layer, anelectron barrier layer, a hole barrier layer, an electron injectionlayer, an electron transporting layer and an exciton barrier layer. Thehole transporting layer may be a hole injection and transporting layerhaving a hole injection function, and the electron transporting layermay be an electron injection and transporting layer having an electroninjection function. A specific structural example of an organicelectroluminescent device is shown in FIG. 1. In FIG. 1, the numeral 1denotes a substrate, 2 denotes an anode, 3 denotes a hole injectionlayer, 4 denotes a hole transporting layer, 5 denotes a light-emittinglayer, 6 denotes an electron transporting layer, and 7 denotes acathode.

The members and the layers of the organic electroluminescent device willbe described below. The descriptions for the substrate and thelight-emitting layer may also be applied to the substrate and thelight-emitting layer of the organic photoluminescent device.

Substrate

The organic electroluminescent device of the invention is preferablysupported by a substrate. The substrate is not particularly limited andmay be those that have been commonly used in an organicelectroluminescent device, and examples thereof used include thoseformed of glass, transparent plastics, quartz and silicon.

Anode

The anode of the organic electroluminescent device used is preferablyformed of as an electrode material a metal, an alloy or anelectroconductive compound each having a large work function (4 eV ormore), or a mixture thereof. Specific examples of the electrode materialinclude a metal, such as Au, and an electroconductive transparentmaterial, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A materialthat is amorphous and is capable of forming a transparentelectroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. Theanode may be formed in such a manner that the electrode material isformed into a thin film by such a method as vapor deposition orsputtering, and the film is patterned into a desired pattern by aphotolithography method, or in the case where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In alternative, inthe case where a material capable of being applied as a coating, such asan organic electroconductive compound, is used, a wet film formingmethod, such as a printing method and a coating method, may be used. Inthe case where emitted light is to be taken out through the anode, theanode preferably has a transmittance of more than 10%, and the anodepreferably has a sheet resistance of several hundred Ohm per square orless. The thickness thereof may be generally selected from a range offrom 10 to 1,000 nm, and preferably from 10 to 200 nm, while dependingon the material used.

Cathode

The cathode is preferably formed of as an electrode material a metal(referred to as an electron injection metal), an alloy or anelectroconductive compound each having a small work function (4 eV orless), or a mixture thereof. Specific examples of the electrode materialinclude sodium, a sodium-potassium alloy, magnesium, lithium, amagnesium-copper mixture, a magnesium-silver mixture, amagnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminummixture, and a rare earth metal. Among These, a mixture of an electroninjection metal and a second metal that is a stable metal having alarger work function than the electron injection metal, for example, amagnesium-silver mixture, a magnesium-aluminum mixture, amagnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, alithium-aluminum mixture, and aluminum, are preferred from thestandpoint of the electron injection property and the durability againstoxidation and the like. The cathode may be produced by forming theelectrode material into a thin film by such a method as vapor depositionor sputtering. The cathode preferably has a sheet resistance of severalhundred Ohm per square or less, and the thickness thereof may begenerally selected from a range of from 10 nm to 5 μm, and preferablyfrom 50 to 200 nm. For transmitting the emitted light, any one of theanode and the cathode of the organic electroluminescent device ispreferably transparent or translucent, thereby enhancing the lightemission luminance.

The cathode may be formed with the electroconductive transparentmaterial described for the anode, thereby forming a transparent ortranslucent cathode, and by applying the cathode, a device having ananode and a cathode, both of which have transmittance, may be produced.

Light-Emitting Layer

The light-emitting layer is a layer, in which holes and electronsinjected from the anode and the cathode, respectively, are recombined toform excitons, and then the layer emits light. A light-emitting materialmay be solely used as the light-emitting layer, but the light-emittinglayer preferably contains a light-emitting material and a host material.The light-emitting material used may be one kind or two or more kindsselected, from the group of compounds represented by the general formula(1) of the invention. In order that the organic electroluminescentdevice and the organic photoluminescent device of the invention exhibita high light emission efficiency, it is important that the singletexcitons and the triplet excitons generated in the light-emittingmaterial are confined in the light-emitting material. Accordingly, ahost material is preferably used in addition to the light-emittingmaterial in the light-emitting layer. The host material used may be anorganic compound that has excited singlet energy and excited tripletenergy, at least one of which is higher than those of the light-emittingmaterial of the invention. As a result, the singlet excitons and thetriplet excitons generated in the light-emitting material of theinvention are capable of being confined in the molecules of thelight-emitting material of the invention, thereby eliciting the lightemission efficiency thereof sufficiently. There may be cases where ahigh light emission efficiency is obtained even though the singletexcitons and the triplet excitons may not be confined sufficiently, andtherefore a host material capable of achieving a high light emissionefficiency may be used in the invention without any particularlimitation. In the organic light-emitting device and the organicelectroluminescent device of the invention, the light emission occurs inthe light-emitting material of the invention contained in thelight-emitting layer. The emitted light contains both fluorescent lightand delayed fluorescent light. However, a part of the emitted light maycontain emitted light from the host material, or the emitted light maypartially contain emitted light from the host material.

In the case where the host material is used, the amount of the compoundof the invention as the light-emitting material contained in thelight-emitting layer is preferably 0.1% by weight or more, and morepreferably 1% by weight or more, and is preferably 50% by weight orless, more preferably 20% by weight or less, and further preferably 10%by weight or less.

The host material in the light-emitting layer is preferably an organiccompound that has a hole transporting function and an electrontransporting function, presents the emitted light from being increasedin wavelength, and has a high glass transition temperature.

Injection Layer

The injection layer is a layer that is provided between the electrodeand the organic layer, for decreasing the driving voltage and enhancingthe light emission luminance, and includes a hole injection layer and anelectron injection layer, which may be provided between the anode andthe light-emitting layer or the hole transporting layer and between thecathode and the light-emitting layer or the electron transporting layer.The injection layer may be provided depending on necessity.

Barrier Layer

The barrier layer is a layer that is capable of inhibiting charges(electrons or holes) and/or excitons present in the light-emitting layerfrom being diffused outside the light-emitting layer. The electronbarrier layer may be disposed between the light-emitting layer and thehole transporting layer, and inhibits electrons from passing through thelight-emitting layer toward the hole transporting layer. Similarly, thehole barrier layer may be disposed between, the light-emitting layer andthe electron transporting layer, and inhibits holes from passing throughthe light-emitting layer toward the electron transporting layer. Thebarrier layer may also be used for inhibiting excitons from beingdiffused outside the light-emitting layer. Thus, the electron barrierlayer and the hole barrier layer each may also have a function as anexciton barrier layer. The electron barrier layer or the exciton barrierlayer referred herein means a layer that has both the functions of anelectron barrier layer and an exciton barrier layer by one layer.

Hole Barrier Layer

The hole barrier layer has the function of an electron transportinglayer in a broad sense. The hole barrier layer has a function ofinhibiting holes from reaching the electron transporting layer whiletransporting electrons, and thereby enhances the recombinationprobability of electrons and holes in the light-emitting layer. As thematerial for the hole barrier layer, the materials for the electrontransporting layer described later may be used depending on necessity.

Electron Barrier Layer

The electron barrier layer has the function or transporting holes in abroad sense. The election barrier layer has a function of inhibitingelectrons from reaching the hole transporting layer while transportingholes, and thereby enhances tine recombination probability of electronsand holes in the light-emitting layer.

Exciton Barrier Layer

The exciton barrier layer is a layer for inhibiting excitons generatedthrough recombination of holes and electrons in the light-emitting layerfrom being diffused to the charge transporting layer, and the use of thelayer inserted enables effective confinement of excitons in thelight-emitting layer, and thereby enhances the light emission efficiencyof the device. The exciton barrier layer may be inserted adjacent to thelight-emitting layer on any of the side of the anode and the side of thecathode, and on both the sides. Specifically, in the case where theexciton barrier layer is present on the side of the anode, the layer maybe inserted between the hole transporting layer and the light-emittinglayer and adjacent to the light-emitting layer, and in the case wherethe layer is inserted on the side of the cathode, the layer may beinserted between the light-emitting layer and the cathode and adjacentto the light-emitting layer. Between the anode and the exciton barrierlayer that is adjacent to the light-emitting layer on the side of theanode, a hole injection layer, an electron barrier layer and the likemay be provided, and between the cathode and the exciton barrier layerthat is adjacent to the light-emitting layer on the side of the cathode,an electron injection layer, an electron transporting layer, a holebarrier layer and the like may be provided. In the case where thebarrier layer is provided, the material used for the barrier layerpreferably has excited singlet energy and excited triplet energy, atleast one of which is higher than the excited singlet energy and theexcited triplet energy of the light-emitting material, respectively.

Hole Transporting Layer

The hole transporting layer is formed of a hole transporting materialhaving a function of transporting holes, and the hole transporting layermay be provided as a single layer or plural layers.

The hole transporting material has one of injection or transportingproperty of holes and barrier property of electrons, and may be any ofan organic material and an inorganic material. Examples of known holetransporting materials that may be used herein include a triazolederivative, an oxadiazole derivative, an imidazole derivative, acarbazole derivative, an indolocarbazole derivative, a polyarylalkanederivative, a pyrazoline derivative, a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, an oxazole derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an anilinecopolymer and an electroconductive polymer oligomer, particularly athiophene oligomer. Among these, a porphyrin compound, an aromatictertiary amine compound and a styrylamine compound are preferably used,and an aromatic tertiary amine compound is more preferably used.

Electron Transporting Layer

The electron transporting layer is formed of a material having afunction of transporting electrons, and the electron, transporting layermay be provided as a single layer or plural layers.

The electron transporting material (which may also function as a holebarrier material in some cases) may have a function of transportingelectrons, which are injected from the cathode, to the light-emittinglayer. Examples of the electron transporting layer that may be usedherein include a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethaneand anthrone derivatives, and an oxadiazole derivative. The electrontransporting material used may be a thiadiazole derivative obtained byreplacing the oxygen atom of the oxadiazole ring of the oxadiazolederivative by a sulfur atom, or a quinoxaline derivative having aquinoxaline ring, which is known as an electron attracting group.Furthermore, polymer materials having these materials introduced to thepolymer chain or having these materials used as the main chain of thepolymer may also be used.

In the production of the organic electroluminescent device, the compoundrepresented by the general formula (1) may be used not only in thelight-emitting layer but also in the other layers than thelight-emitting layer. In this case, the compound represented by thegeneral formula (1) used to the light-emitting layer and the compoundrepresented by the general formula (1) used in the other layers than thelight-emitting layer may be the same as or different from each other.For example, the compound represented by the general formula (1) may beused in the injection layer, the barrier layer, the hole barrier layer,the electron barrier layer, the exciton barrier layer, the holetransporting layer, the electron transporting layer and the likedescribed above. The film forming method of the layers are notparticularly limited, and the layers may be produced by any of a dryprocess and a wet process.

Specific examples of preferred materials that may be used in the organicelectroluminescent device are shown below, but the materials that may beused in the invention are not construed as being limited to the examplecompounds. The compound that is shown as a material having a particularfunction may also be used as a material having another function. In thestructural formulae of the example compounds, R, R′ and R₁ to R₁₀ eachindependently represent a hydrogen atom or a substituent; X represents acarbon atom or a heteroatom that forms a cyclic structure; n representsan integer of from 3 to 5; Y represents a substituent; and m representsare integer of 0 or more.

Preferred examples of a compound that may also be used as the hostmaterial of the light-emitting layer are shown below.

Preferred examples of a compound that may be used as the hole injectionmaterial are shown below.

Preferred examples of a compound that may be used as the holetransporting material are shown below.

Preferred, examples of a compound that may be used as the electronbarrier material are shown below.

Preferred examples of a compound that may be used as the hole barriermaterial are shown below.

Preferred examples of a compound that may be used as the electrontransporting material are shown below.

Preferred examples of a compound that may be used as the electroninjection material are shown below.

Preferred examples of a compound as a material that may be added areshown below. For example, the compound may be added as a stabilizingmaterial.

The organic electroluminescent device thus produced by theaforementioned method emits light on application of an electric fieldbetween the anode and the cathode of the device. In this case, when thelight emission is caused by the excited single energy, light having awavelength that corresponds to the energy level thereof may be confirmedas fluorescent light and delayed fluorescent light. When the lightemission is caused by the excited triplet energy, light having awavelength that corresponds to the energy level thereof may be confirmedas phosphorescent light. The normal fluorescent light has a shorterlight emission lifetime than the delayed fluorescent light, and thus thelight emission lifetime may be distinguished between the fluorescentlight and the delayed fluorescent light.

The phosphorescent light may substantially not observed with a normalorganic compound, such as the compound of the invention, at roomtemperature since the excited triplet energy is converted to heat or thelike due to the instability thereof, and is immediately deactivated witha short lifetime. The excited triplet energy of the normal organiccompound may be measured by observing light emission under an extremelylow temperature condition.

The organic electroluminescent device of the invention may be applied toany of a single device, a device having a structure with plural devicesdisposed in an array, and a device having anodes and cathodes disposedin an X-Y matrix. According to the invention, an organic light-emittingdevice that is largely improved in light emission efficiency may beobtained by adding the compound represented by the general formula (1)in the light-emitting layer. The organic light-emitting device such asthe organic electroluminescent device, of the invention may be appliedto a further wide range of purposes. For example, an organicelectroluminescent display apparatus may be produced with the organicelectroluminescent device of the invention, and for the details thereof,reference may be made to S. Tokito, C. Adachi and H. Murata, “Yuki ELDisplay” (Organic EL Display) (Ohmsha, Ltd.). In particular, the organicelectroluminescent device of the invention may be applied to organicelectroluminescent illumination and backlight which are highly demanded.

EXAMPLE

The features of the invention will be described more specifically withreference to synthesis examples and working examples below. Thematerials, processes, procedures and the like shown below may beappropriately modified unless they deviate from the substance of theinvention. Accordingly, the scope of the invention is not construed asbeing limited to the specific examples shown below.

Synthesis Example 1

In this synthesis example, a compound 1 was synthesized according to thefollowing scheme. Cz represents a 9-carbazolyl group.

480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 80 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.67 g (10.0 mmol) of 9H-carbazole was added to themixture, which was stirred under a nitrogen stream at room temperaturefor 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroterephthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, 5.0 mL of water was added to the mixture, which was thenstirred. After stirring, N,N-dimethylformamide was removed from themixture. After the removal, 200 mL of water was added to the mixture, towhich ultrasonic waves were applied. After the application, the mixturewas suction-filtered to provide a solid matter. The resulting solidmatter was purified by silica gel column chromatography. In the columnchromatography, chloroform was firstly used as a developing solvent, andthen acetone gas used as a developing solvent. The resulting fractionwas concentrated to provide a solid matter, which was then rinsed with amixed solvent of chloroform and acetone, thereby providing a yellowpowdered solid matter in a yield amount of 1.05 g and a yield of 66.5%.

¹H-NMR (500 MHz, DMSO-d₆, ppm): δ 7.93-7.89 (m, 16H), 7.26 (t, J=7.8 Hz,8H), 7.16 (t, J=7.8 Hz, 8H)

Elemental analysis: calculated: C 85.26, H 4.09, N 10.65; found: C85.28, H 4.11, N 10.61

Synthesis Example 2

In this synthesis example, a compound 4 was synthesized according to thefollowing scheme.

480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100-mLthree-neck flash, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.95 g (10.0 mmol) of 3,6-dimethyl-9H-carbazole was addedto the mixture, which was stirred under a nitrogen stream at roomtemperature for 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroterephthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen stream at 60° C. for 10 hours. Afterstirring, the mixture was added to 400 mL of water, which was thenstirred. After stirring, the mixture was suction-filtered to provide asolid matter. The resulting solid matter was rinsed with methanol,thereby providing an orange powdered solid matter in a yield amount of1.68 g and a yield of 93.2%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.81 (d, J=8.5 Hz, 8H), 7.71 (s, 8H),7.11 (d, J=8.5 Hz, 8H), 2.37 (s, 24H)

Elemental analysis: calculated for C₆₄H₄₈N₆: C 85.30, H 5.37, N 9.33%,found: C 85.39, H 5.36, N 9.35%

Synthesis Example 3

In this synthesis example, a compound 6 was synthesized according to thefollowing scheme.

480 mg (12.0 mmol) of 60% of sodium hydride was placed in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 2.79 g (10.0 mmol) of 3,6-di-tert-butyl-9H-carbazole wasadded to the mixture, which was stirred under a nitrogen stream at roomtemperature for 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroterephthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, the mixture was added to 400 mL of water, which was thenstirred. After stirring, the mixture was suction-filtered to provide asolid matter. The resulting solid matter was purified by silica gelcolumn chromatography. In the column chromatography, chloroform wasfirstly used as a developing solvent, and then acetone was used as adeveloping solvent. The resulting fraction was concentrated to provide asolid matter, which was then rinsed with a mixed solvent of chloroformand acetone, thereby providing an orange powdered solid matter in ayield amount of 400 mg and a yield of 16.1%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.77 (d, J=1.5 Hz, 8H), 7.43 (d, J=8.5Hz, 8H), 7.08 (dd, J=8.8 Hz, 1.5 Hz, 8H), 1.35 (s, 72H)

Elemental analysis: calculated for C₈₈H₃₆N₆: C 85.39, H 7.82, N 6.79%,found: C 85.38, H 7.82, N 6.78%

Synthesis Example 4

In this synthesis example, a compound 301 was synthesized according tothe following scheme.

480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL, of N,N-dimethylformamide was added thereto,followed by stirring. 1.67 g (10.0 mmol) of 9H-carbazole was added tothe mixture, which was stirred under a nitrogen stream at roomtemperature for 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroisophthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen atmosphere at 60° C. for 10 hours. Afterstirring, 5.0 mL of water was added to the mixture, which was thenstirred. After stirring, N,N-dimethylformamide was removed from themixture. After the removal, 200 mL of water was added to the mixture, towhich ultrasonic waves were applied. After the application, the mixturewas suction-filtered to provide a solid matter. The resulting solidmatter was purified by silica gel column chromatography. In the columnchromatography, a mixed solvent of chloroform and hexane (1/5) wasfirstly used as a developing solvent, and then a mixed solvent ofchloroform and hexane (1/2) was used as a developing solvent. Theresulting fraction was concentrated to provide a solid matter, which wasthen recrystallized from a mixed solvent of acetone, and hexane, therebyproviding a yellow powdered solid matter in a yield amount of 311 mg anda yield of 19.7%.

¹NMR (500 MHz, aetone-d₆, ppm): δ 8.33 (d, J=7.7 Hz, 2H), 8.06 (d, J=8.2Hz, 2H), 7.84-7.82 (m, 4H), 7.71-7.66 (m, 6H), 7.49-7.45 (m, 4H), 7.43(d, J=7.6 Hz, 2H), 7.14-7.08 (m, 8H), 6.816 (t, J=7.3 Hz, 2H), 6.71 (t,J=7.7 Hz, 2H)

Elemental analysis: calculated: C 85.26, H 4.09, N 10.65; found: C85.22, H 4.03, N 10.62

Synthesis Example 5

In this synthesis example, a compound 392 was synthesized according tothe following scheme.

480 mg (12.0 mmol) of 60% sodium hydride was pieced in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.67 g (10.0 mmol) of 9H-carbazole was added to themixture, which was stirred under a nitrogen stream at room temperaturefor 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroisophthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, 5.0 mL of water was added to the mixture, which was thenstirred. After stirring, N,N-dimethylformamide was removed from themixture. After the removal, 200 mL of water was added to the mixture, towhich ultrasonic waves were applied. After the application, the mixturewas suction-filtered to provide a solid matter. The resulting solidmatter, was purified by silica gel column chromatography. In the columnchromatography, chloroform was firstly used as a developing solvent, andthen a mixed solvent of chloroform and acetone (1/2) was used as adeveloping solvent. The resulting fraction was concentrated to provide asolid matter, which was then rinsed with methanol, thereby providing apale yellow powdered solid matter in a yield amount of 600 mg and ayield of 46.9%.

Synthesis Example 6

In this synthesis example, a compound 501 was synthesized according tothe following scheme. Cz represents a 9-carbazolyl group.

480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.67 g (10.0 mmol) of 9H-carbazole was added to themixture, which was stirred under a nitrogen stream at room temperaturefor 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluorophthalonitrile was added to the mixture, and the mixture wasstirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, 5.0 ml of water was added to the mixture, which was thenstirred. After stirring, N,N-dimethylformamide was removed from themixture. After the removal, 200 mL of water was added to the mixture, towhich ultrasonic waves were applied. After the application, the mixturewas suction-filtered to provide a solid matter. The resulting solidmatter was purified by silica gel column chromatography. In the columnchromatography, chloroform was firstly used as a developing solvent, andthen a mixed solvent of acetone and chloroform (1/2) was used as adeveloping solvent. The resulting fraction was concentrated to provide asolid matter, which was then recrystallized from a mixed solvent ofchloroform and methanol, thereby providing a yellow powdered solidmatter in a yield amount of 450 mg and a yield of 28.5%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.90-7.87 (m, 4H), 7.72-7.70 (m, 4H),7.40-7.37 (m, 8H), 7.16-7.10 (m, 8H), 6.74 (t, J=7.7 Hz, 4H), 6.60 (t,J=7.7 Hz, 4H)

Elemental analysis: calculated: C 85.26, H 4.09, N 10.65; found: C85.16, H 4.02, N 10.55

Synthesis Example 7

In this synthesis example, a compound 504 was synthesized according tothe following scheme.

480 mg (12.0 mmol) of 60% sodium hydride was placed in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.95 g (10.0 mmol) of 3,6-dimethyl-9H-carbazole was addedto the mixture, which was stirred under a nitrogen stream at roomtemperature for 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluorophthalonitrile was added to the mixture, and the mixture wasstirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, the mixture was added to 400 mL of water, which was thenstirred. After stirring, the mixture was suction-filtered to provide asolid matter. The resulting solid matter was purified by silica gelcolumn chromatography. In the column chromatography, chloroform wasfirstly used as a developing solvent, and then a mixed solvent ofchloroform and acetone (1/2) was need as a developing solvent. Theresulting fraction was concentrated to provide a solid matter, which wasthen rinsed with acetone, thereby providing an orange powdered solidmatter in a yield amount of 515 mg and a yield of 28.6%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.64 (s, 4H), 7.54 (d, J=8.5 Hz, 4H),7.27 (d, J=8.5 Hz, 4H), 7.15 (s, 4H), 6.95 (dd, J=8.3 Hz, 1.5 Hz, 4H),6.44 (dd, J=8.5 Hz, 1.5 Hz, 4H), 2.34 (s, 12H), 2.10 (s, 12H)

Elemental analysis: calculated for C 85.30, H 5.37, N 9.33; found: C85.34, H 5.35, N 9.30

Synthesis Example 8

In this synthesis example, a compound 901 was synthesized according tothe following scheme.

480 mg (12.0 mmol) of 10% sodium hydride was placed in a 100-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 40 mL of N,N-dimethylformamide was added thereto, followedby stirring. 1.71 g (10.0 mmol) of 1,2,3,4-tetrahydrocarbazole was addedto the mixture, which was stirred under a nitrogen stream at roomtemperature for 30 minutes. After stirring, 400 mg (2.00 mmol) oftetrafluoroterephthalonitrile was added to the mixture, and the mixturewas stirred under a nitrogen atmonphere at 60° C. for 10 hours. Afterstirring, the mixture was added to 400 mL of water, which was thenstirred. After stirring, the mixture was suction-filtered to provide asolid matter. The resulting solid matter was purified by silica gelcolumn chromatography. In the column chromatography, chloroform wasfirstly used as a developing solvent, and then acetone was used as adeveloping solvent. The resulting fraction was concentrated to provide asolid matter which was then rinsed with a mixed solvent of chloroformand acetone, thereby providing an orange powdered solid matter in ayield amount of 120 mg and a yield of 7.4%.

Synthesis Example 9

In this synthesis example, a compound 252 was synthesized according tothe following scheme.

480 mg (12.0 mmol) of 60% sodium hydride was rinsed with hexane, andthen added to a dried THF solution of 3.20 g (10.0 mmol) of3,6-diphenylcarbazole, which was being stirred under a nitrogenatmosphere, at room temperature. After stirring for 30 minutes, 400 mg(2.00 mmol) of tetrafluoroterephthalonitrile was added to the mixture,and the mixture was stirred under a nitrogen atmonphere at roomtemperature for 10 hours. Thereafter, the reaction was terminated with 5mL of water, and the mixture was concentrated under reduced pressure toprovide a yellow solid matter. The resulting solid matter was purifiedby silica gel chromatography with chloroform as a developing solvent,thereby providing an orange powdered solid matter in a yield amount of2.20 g and a yield of 79%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 8.37 (d, J=1.5 Hz, 8H), 8.05 (d, J=8.5Hz, 8H), 7.70 (m, 16H), 7.62 (dd, J=8.5, 1.5 Hz, 8H), 7.45 (m, 16H),7.36 (m, 8H)

IR (KBr, cm⁻¹): 2,236, 2,228, 1,600, 1,476, 1,456, 1,441, 1,290, 1,226

MALDI-TOFMS (m/z): [M]⁺ C₁₀₄H₆₄ N₆: calculated: 1,396.52; found:1,396.66

Elemental analysis: calculated: C 89.37, H 4.62, N 6.01; found: C 89.26,H 4.53, N 5.95

Synthesis Example 10

In this synthesis example, a compound 523 was synthesized according tothe following scheme.

1.52 g (9.14 mmol) 9H-carbazole and 1.91 g (13.7 mol) of potassiumcarbonate were placed in a 50-mL recovery flask, and the interior of theflask was substituted with nitrogen. 15 mL of dimethylsulfoxide wasadded to the mixture, which was stirred under a nitrogen stream at roomtemperature for 1 hour. 0.500 g (3.05 mmol) of4,5-difluorophthalonitrile was added to the mixture. The mixture wasstirred under a nitrogen stream at room temperature for 3 hours and thenat 50° C. for 20 hours. Thereafter, the mixture was added to water,followed by stirring. The mixture was extracted with toluene. After theextraction, the extracted solution was rinsed with a saturated sodiumchlorine aqueous solution. After rinsing, an organic layer and anaqueous layer were separated, and the organic layer was dried by addingmagnesium sulfate thereto. After drying, the mixture wassuction-filtered to provide a filtrate. The resulting filtrate wasconcentrated to provide a solid matter, which was purified by silica gelcolumn chromatography. In the purification, a mixed solvent of tolueneand hexane (1/4) was firstly used as a developing solvent, then a mixedsolvent of toluene and hexane (7/3) was used, and then toluene was usedas a developing solvent (the developing ratio was gradually changed).The resulting fraction was concentrated to provide a solid matter, whichwas then rinsed by reslurry with a mixed solvent of acetone andmethanol, thereby providing a pale yellow powdered solid matter in ayield amount of 1.20 g and a yield of 85.8%.

¹H NMR (500 MHz, acetone-d₆, ppm): δ 8.73 (s, 2H), 7.91-7.89 (m, 4H),7.40-7.38 (m, 4H), 7.13-7.09 (m, 8H)

MS (MALDI): m/z calculated: 458.15 [M+H]⁺; found: 458.12

Synthesis Example 11

In this synthesis example, a compound 31 was synthesized according tothe following scheme.

The compound b and the compound c were synthesized in the same manner asin J-Z. Cheng et al., tetrahedron, 67 (2011), 734.

2,5-Dibromoterephthalonitrile as the compound c (1.44 g, 5.0 mol),9H-carbazole (1.89 g, 11.3 mol), copper powder (0.64 g, 10 mol),potassium carbonate (2.79 g, 20 mol), 18-crown-6 (0.25 g, 0.94 mol) andDMSO (5 mL) were placed in a two-neck flask under a nitrogen atmosphere,and stirred at 140° C. for 9 hours. Thereafter, impurities were removedfrom the reaction product by dissolving the product in chloroform,followed by filtering, and the reaction product was rinsed with waterand dried over magnesium sulfate. Thereafter, the reaction product waspurified by column chromatography (chloroform), thereby providing yellowpowder in a yield amount of 0.53 g and a yield of 23%.

Synthesis Example 12

In this synthesis example, a compound 716 was synthesized according tothe following scheme.

4.01 g (20.8 mmol) of 3-phenyl-1H-indole and 5.72 g (41.4 mmol) ofpotassium carbonate were placed in a 50 mL three-neck flask, and theinterior of the flask was substituted by nitrogen. 20 mL ofdimethylsulfoxide was added to the mixture, which was then stirred atroom temperature for 1 hour. After cooling the mixture with an ice bath,0.696 g (3.48 mmol) of tetrafluoroterephthalonitrile was added to themixture, and the mixture was then stirred at a temperature of 0° C.,which was gradually increased to room temperature. The mixture wasstirred under a nitrogen atmosphere at room, temperature for 24 hours.After stirring, the mixture was added to approximately 300 mL of water,followed by stirring. After stirring, the mixture was suction-filteredto provide a solid matter. The resulting solid matter was dissolved andpurified by silica gel column chromatography. In the columnchromatography, a mixed solvent of toluene and hexane (1/5) was firstlyused as a developing solvent, and then toluene was used as a developingsolvent. The resulting fractions was concentrated to provide a solidmatter, which was then rinsed with a mixed solvent of acetone andmethanol, thereby providing an orange powdered solid matter in a yieldamount of 2.02 g and a yield of 65.0%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.73 (s, 4H), 7.67 (d, J=8.0 Hz, 4H),7.51-7.33 (m, 24H), 7.09 (t, J=7.8 Hz, 4H), 7.02 (t, J=7.5 Hz, 4H)

Synthesis Example 13

In this synthesis example, a compound 728 was synthesized according tothe following scheme.

2.40 g (60.0 mmol) of 60% sodium hydride was placed in a 200-mLthree-neck flask, the interior of the flask was substituted withnitrogen, and 100 mL of tetrahydrofuran was added thereto, followed bystirring. 9.65 g (50.0 mmol) of 2-phenyl-1H-indole was added to themixture, which was stirred under a nitrogen stream at room temperaturefor 30 minutes. 2.00 g (10.0 mmol) of tetrafluoroterephthalonitrile wasadded to the mixture, and the mixture was stirred under a nitrogenatmonphere at room temperature for 24 hours. After stirring,approximately 50 mL of water was gradually added to the mixture,followed by stirring. After stirring, an organic layer and an aqueouslayer were separated, and the aqueous layer was extracted with toluene.The organic layer and the extracted solution were combined to each otherand rinsed with a saturated sodium chloride aqueous solution. Afterrinsing, the organic layer was dried by adding magnesium sulfatethereto. After drying, the mixture was suction-filtered to provide afiltrate. The resulting filtrate was concentrated to provide a solidmatter, which was dissolved in chloroform, and the solution wassuction-filtered through Celite and silica gel to provide a filtrate.The resulting filtrate was concentrated to provide a solid matter, whichwas rinsed with isopropanol. After rinsing, the solid matter was rinsedwith ethyl acetate, thereby providing an orange powdered solid matter ina yield amount of 1.70 g and a yield of 19.0%.

¹H NMR (500 MHz, DMSO-d₆, ppm): δ 7.48 (d, J=8.0 Hz, 4H), 7.33 (t, J=7.0Hz, 4H), 7.26 (t, J=7.0 Hz, 8H), 7.09 (t, J=7.0 Hz, 4H), 6.99 (d, J=8.0Hz, 4H), 6.81 (t, J=8.0 Hz, 4H), 6.65 (s, 4H), 6.53 (d, J=7.0 Hz, 8H)

Example 1

In this example, a toluene solution of the compound 1 synthesized inSynthesis Example 1 was prepared and irradiated with light having awavelength of 280 nm at 300 K under bubbling with nitrogen, and thus thelight emission wavelength shown in Table 7 was observed. The timeresolved spectrum was obtained with Streak Camera, Model C4334, producedby Hamamatsu Photonics K.K., and the component with a short lightemission lifetime was designated as fluorescent light, whereas thecomponent with a long light emission lifetime was designated as delayedfluorescent light (FIG. 2). The lifetimes of the fluorescent lightcomponent and the delayed fluorescent light component were as shown inTable 7.

The results of the same evaluation with the compounds synthesized inSynthesis Examples 2 to 7 instead of the compound 1 are also shown inTable 7. The compound 392 and the compound 901 were measured withoutbubbling with nitrogen.

TABLE 7 Delayed Light emission Fluorescent fluorescent wavelength lightlight Compound (nm) component (ns) component (μs) Compound 1 537 8.761.91 Compound 4 556 9.58 1.53 Compound 6 553 3.53 8.46 Compound 31 48022.5 65.5 Compound 252 577 9.0 1.10 Compound 301 508 3.77 4.89 Compound392 488 10.78 3.65 Compound 501 525 12.96 13.45 Compound 504 521 18.816.57 Compound 523 473 28.52 129.67 Compound 901 556 10.00 3.54

Example 2

In this example, an organic photoluminescent device having alight-emitting layer formed of the compound 1 and a host material wasproduced and evaluated for the characteristics thereof.

On a silicon substrate, the compound 1 and mCP were vapor-deposited fromseparate vapor deposition sources respectively by a vacuum vapordeposition method under condition of a vacuum degree of 5.0×10⁻⁴ Pa,thereby forming a thin film having a thickness of 100 nm and aconcentration of the compound 1 of 6.0% by weight at a rate of 0.3nm/sec, which was designated as an organic photoluminescent device. Thelight emission spectrum of the thin film on irradiating the device withlight having a wavelength of 337 nm with an N₂ laser was evaluated at300 K with Absolute Quantum Yield Measurement System, Model C9920-02,produced by Hamamatsu Photonics K.K., and thus light emission with awavelength of 548 nm was observed with a photoluminescence quantumefficiency of 47%. Subsequently, the time resolved spectra onirradiating the device with light having a wavelength of 337 nm with anN₂ laser at temperatures of 20 K, 50 K, 100 K, 150 K, 200 K, 250 K and300 K were evaluated with a streak camera, Model C4334, produced byHamamatsu Photonics K.K. and the component with a short light emissionlifetime was designated as fluorescent light, whereas the component witha long light emission lifetime was designated as delayed fluorescentlight. As a result, the fluorescent light component and the delayedfluorescent light component were observed in a range of from 50 to 500 K(FIG. 3). The light emission lifetime of the fluorescent light componentwas from 12 to 16 nm, and that of the delayed fluorescent lightcomponent was 11 μs at 100 K and 8.8 μs at 150 K.

The same test was performed with organic photoluminescent devicesproduced with the compound 501 and the compound 289 instead of thecompound 1, and as a result, the fluorescent light component and thedelayed fluorescent light component were similarly observed.

Example 3

In this example, an organic electroluminescent device having alight-emitting layer formed of the compound 1 and CBP was produced andevaluated for the characteristics thereof.

Thin films each were formed by a vacuum vapor deposition method at avacuum degree of 5.0×10⁻⁴ Pa on a glass substrate having formed thereonan anode formed of indium tin oxide (ITO) having a thickness of 100 nm.First, α-NPD was formed to a thickness of 35 nm on ITO. The compound 1and CBP were then vapor-deposited from separate vapor deposition sourcesrespectively to form a layer having a thickness of 15 nm, which wasdesignated as a light-emitting layer. The concentration of the compound1 herein was 6.0% by weight. TPBi was then formed to a thickness of 65nm, lithium fluoride (LiF) was further vapor-deposited to a thickness of0.8 nm, and then aluminum (Al) was vapor-deposited to a thickness of 80nm, which was designated as a cathode, thereby completing an organicelectroluminescent device.

The organic electroluminescent device thus produced was measured withSemiconductor Parameter Analyzer (E5273A, produced by AgilentTechnologies, Inc.), Optical Power Meter (1930C, produced by NewportCorporation) and Fiber Optic Spectrometer (USB2000, produced by OceanOptics, Inc.), and thus light emission of a wavelength of 544 nm wasobserved. The electric current density-voltage (J-V) characteristics areshown in FIG. 4, and the electric current density-external quantumefficiency characteristics are shown in FIG. 5. The organicelectroluminescent device using the compound 1 as a light emissionmaterial achieved a high external quantum efficiency of 17.06%.

Example 4

An organic photoluminescent device was produced by using the compound 6instead of the compound 1 in Example 3 and subjected to the same test,and thus light emission of a wave length of 553 nm was observed. Theelectric current density-external quantum efficiency characteristics areshown in FIG. 6.

Example 5

An organic photoluminescent device was produced by using the compound301 instead of the compound 1 in Example 3 and subjected to the sametest, and thus light emission of a wavelength of 513 as was observed.The electric current density-external quantum efficiency characteristicsare shown in FIG. 7. The organic electroluminescent device using thecompound 301 as a light emission material achieved a high externalquantum efficiency of 19.32%.

Example 6

An organic photoluminescent device was produced by using the compound501 instead at the compound 1 in Example 3 and subjected to the sametest, and thus light emission of a wavelength of 530 nm was observed.The electric current density-voltage (J-V) characteristics are shown inFIG. 8, and the electric current density-external quantum efficiencycharacteristics are shown in FIG. 9. The organic electroluminescentdevice using the compound 501 as a light emission material achieved ahigh external quantum efficiency of 17.84%.

Example 7

In this example, an organic electroluminescent device having alight-emitting layer containing the compound 252 synthesized inSynthesis Example 9 as a light-emitting material was produced andevaluated for the characteristics thereof.

Thin films each were formed by a vacuum vapor deposition method at avacuum degree of 5.0×10⁻⁴ Pa on a glass substrate having formed thereonan anode formed of indium tin oxide (ITO) having a thickness of 100 nm.First, α-NPD was formed to a thickness of 35 nm on ITO. The compound 252and CBP were then vapor-deposited from separate vapor deposition sourcesrespectively to form a layer having a thickness of 15 nm, which wasdesignated as a light-emitting layer. The concentration of the compound252 herein was 6.0% by weight. TPBi was then formed to a thickness of 65nm, lithium fluoride (LiF) was further vapor-deposited to a thickness of0.8 nm, and then aluminum (Al) was vapor-deposited to a thickness of 80nm, which was designated as a cathode, thereby completing an organicelectroluminescent device.

The organic electroluminescent device thus produced was measured withSemiconductor Parameter Analyser (E5273A, produced by AgilentTechnologies, Inc.), Optical Power Meter (1930C, produced by NewportCorporation) and Fiber Optic Spectrometer (USB2000, produced by OceanOptics, Inc.), and thus the light emission spectrum shown in FIG. 10 wasobserved. The electric current density-voltage (J-V) characteristics areshown in FIG. 11, and the electric current density-external quantumefficiency characteristics are shown in FIG. 12.

Example 8

In this example, an organic electroluminescent device having alight-emitting layer containing the compound 523 synthesized inSynthesis Example 10 as a light-emitting material was produced andevaluated for the characteristics thereof.

Thin films each were formed by a vacuum vapor deposition method at avacuum degree of 5.0×10⁻⁴ Pa on a glass substrate having formed thereonan anode formed of indium tin oxide (ITO) having a thickness of 100 nm.First, α-NPD was formed to a thickness of 40 nm on ITO, and then mCP wasformed to a thickness of 10 nm. The compound 523 and PPT were thenvapor-deposited from separate vapor deposition sources respectively toform a layer having a thickness of 20 nm, which was designated as alight-emitting layer. The concentration of the compound 523 herein was6.0% by weight. PPT was then formed to a thickness of 40 nm, lithiumfluoride (LiF) was further vapor-deposited to a thickness of 0.8 nm, andthen aluminum (Al) was vapor-deposited to a thickness of 80 nm, whichwas designated as a cathode, thereby completing an organicelectroluminescent device.

The organic electroluminescent device thus produced was measured withSemiconductor Parameter Analyser (ES273A, produced by AgilentTechnologies, Inc.), Optical Power Meter (1930C, produced by NewportCorporation) and Fiber Optic Spectrometer (USB2000, produced by OceanOptics Inc.), and thus the light emission spectrum shown in FIG. 13 wasobserved. The electric current density-voltage (J-V) characteristics areshown in FIG. 14, and the electric current density-external quantumefficiency characteristics are shown in FIG. 15.

Example 9

In this example, an organic electroluminescent device having alight-emitting layer containing the compound 31 synthesized in SynthesisExample 11 as a light-emitting material was produced and evaluated forthe characteristics thereof.

Thin films each were formed by a vacuum vapor deposition method at avacuum degree of 5.0×10⁻⁴ Pa on a glass substrate having formed thereonan anode formed of indium tin oxide (ITO) having a thickness of 100 nm.First, α-NPD was formed to a thickness of 35 nm on ITO, and then mCP wasformed to a thickness of 10 nm. The compound 31 and mCP were thenvapor-deposited from separate vapor deposition sources respectively toform a layer having a thickness of 15 nm, which was designated as alight-emitting layer. The concentration of the compound 31 herein was3.0% by weight. PPT was then formed to a thickness of 10 nm, TPBi wasformed thereon to a thickness of 40 nm, lithium fluoride (LiF) wasfurther vapor-deposited to a thickness of 0.8 nm, and then aluminum (Al)was vapor-deposited to a thickness of 100 nm, which was designated as acathode, thereby completing an organic electroluminescent device.

The organic electroluminescent device thus produced was measured withSemiconductor Parameter Analyser (E5273A, produced by AgilentTechnologies, Inc.), Optical Power Meter (1930C, produced by NewportCorporation) and Fiber Optic Spectrometer (USB2000, produced by OceanOptics, Inc.), and thus the light emission spectrum shown in FIG. 16 wasobserved. The electric current density-voltage (J-V) characteristics areshown in FIG. 17, and the electric current density-external quantumefficiency characteristics are shown in FIG. 18.

Example 10

In this example, organic electroluminescent devices having alight-emitting layer containing the compound 1 as a light-emittingmaterial in various concentrations were produced and evaluated for thecharacteristics thereof.

Thin films each were formed by a vacuum vapor deposition method at avacuum degree of 5.0×10⁻⁴ Pa on a glass substrate having formed thereonan anode formed of indium tin oxide (ITO) having a thickness of 100 nm.First, HAT-CN was formed to a thickness of 10 nm on ITO, and thenTris-PCz was formed to a thickness of 30 nm. The compound 1 and mCBPwere then vapor-deposited from separate vapor deposition sourcesrespectively to form a layer having a thickness of 30 nm, which wasdesignated as a light-emitting layer. The concentration of the compound1 herein was 3% by weight, 6% by weight, 10% by weight or 15% by weight.T2T was then formed to a thickness of 10 nm, BPy-TP2 was formed thereonto a thickness of 40 nm, lithium fluoride (LiF) was furthervapor-deposited to a thickness of 0.8 nm, and then aluminum (Al) wasvapor-deposited to a thickness of 100 nm, which was designated as acathode, thereby completing an organic electroluminescent device, forcomparison, an organic electroluminescent device, in which the compound1 in the light-emitting layer was changed to 6% by weight of Ir(ppy)₃,was produced. The organic electroluminescent devices were measured withthe same equipments as in Example 3. The luminance-light emissionefficiency characteristics are shown in FIG. 19, and the luminancedeterioration, characteristics are shown in FIG. 20. The externalquantum efficiency achieved was 17.0% for the case where theconcentration of the compound 1 was 3% by weight, 15.6% for the case of6% by weight, 142% for the case of 10% by weight, and 14.0% for the caseof 15% by weight. In the case where the concentration of the compound 1is 10% by weight, a high external quantum efficiency (13.8%) wasachieved at 1,000 cd/m².

INDUSTRIAL APPLICABILITY

The organic light-emitting device of the invention is capable ofachieving a high light emission efficiency. The compound of theinvention is useful as a light-emitting material of the organiclight-emitting device. Accordingly, the invention has high industrialapplicability.

REFERENCE SIGNS LIST

-   1 substrate-   2 anode-   3 hole Injection layer-   4 hole transporting layer-   5 light-emitting layer-   6 electron transporting layer-   7 cathode

1. A light-emitting material comprising a compound represented by thefollowing general formula (1):

wherein in the general formula (1), at least one of R¹ to R⁵ representsa cyano group, at least one of R¹ to R⁵ represents a group representedby the following general formula (11), and the balance of R¹ to R⁵represents a hydrogen atom or a substituent;

wherein in the general formula (11), R²¹ to R²⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof the following requirements (A) and (B) is satisfied: (A) R²⁵ and R²⁶jointly form a single bond, and (B) R²⁷ and R²⁸ jointly form an atomicgroup that is required for forming a substituted or unsubstitutedbenzene ring.
 2. The light-emitting material according to claim 1, whichemits delayed fluorescent light.
 3. The light-emitting materialaccording to claim 1, wherein at least one of R¹ to R⁵ represents asubstituted or unsubstituted 9-carbazolyl group, a substituted orunsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, a substituted orunsubstituted 1-indolyl group or a substituted or unsubstituteddiarylamino group.
 4. The light-emitting material according to claim 1,wherein at least two of R¹ to R⁵ represent a substituted orunsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group. 5.The light-emitting material according to claim 1, wherein at least oneof R¹ to R⁵ represents a cyano group, and the balance of R¹ to R⁵ eachindependently represents any of a hydroxy group, a halogen atom, asubstituted or unsubstituted 9-carbazolyl group, a substituted orunsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, a substituted orunsubstituted 1-indolyl group or a substituted or unsubstituteddiarylamino group.
 6. The light-emitting material according to claim 1,wherein at least one of R¹ to R⁵ represents a cyano group, and thebalance of R¹ to R⁵ each independently represents any of a substitutedor unsubstituted 9-carbazolyl group, a substituted or unsubstituted1,2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted1-indolyl group or a substituted or unsubstituted diarylamino group. 7.The light-emitting material according to claim 1, wherein at least oneof R¹ to R⁵ represents a cyano group, and the balance of R¹ to R⁵ eachrepresents a substituted or unsubstituted 9-carbazolyl group.
 8. Thelight-emitting material according to claim 1, wherein at least one of R¹to R⁵ represents a hydroxy group, at least one of R¹ to R⁵ represents acyano group, and the balance of R¹ to R⁵ each represents a substitutedor unsubstituted 9-carbazolyl group.
 9. The light-emitting materialaccording to claim 1, wherein at least one of R¹ to R⁵ represents agroup represented by any of the following general formulae (12) to (15):

wherein in the general formula (12), R³¹ to R³⁸ each independentlyrepresent a hydrogen atom or a substituent;

wherein in the general formula (13), R⁴¹ to R⁴⁶ each independentlyrepresent a hydrogen atom or a substituent;

wherein in the general formula (14), R⁵¹ to R⁶² each independentlyrepresent a hydrogen atom or a substituent;

wherein in the general formula (15), R⁷¹ to R⁸⁰ each independentlyrepresent a hydrogen atom or a substituent.
 10. The light-emittingmaterial according to claim 1, which comprises a compound represented bythe following general formula (2):

wherein in the general formula (2), at least one of R¹¹, R¹², R¹⁴ andR¹⁵ represents a cyano group, at least three of R¹¹ to R¹⁵ eachrepresent a substituted or unsubstituted 9-carbazolyl group, asubstituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, asubstituted or unsubstituted 1-indolyl group or a substituted orunsubstituted diarylamino group, and the balance of R¹¹ to R¹⁵represents a hydroxy group.
 11. The light-emitting material according toclaim 1, which comprises a compound represented by the following generalformula (3):

wherein in the general formula (3), one of R⁸¹ to R⁸⁵ represents a cyanogroup, two of R⁸¹ to R⁸⁵ each represent a substituted or unsubstituted9-carbazolyl group, and the other two thereof each represent a hydrogenatom.
 12. A compound represented by the following general formula (2):

wherein in the general formula (2), at least one of R¹¹, R¹², R¹⁴ andR¹⁵ represents a cyano group, at least three of R¹¹ to R¹⁵ eachrepresent a substituted or unsubstituted 9-carbazolyl group, asubstituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, asubstituted or unsubstituted 1-indolyl group or a substituted orunsubstituted diarylamino group, and the balance of R¹¹ to R¹⁵represents a hydroxy group, provided that R¹² is not a cyano group whenR¹⁴ is a cyano group.
 13. An organic light-emitting device comprising asubstrate having thereon a light-emitting layer containing thelight-emitting material which comprises a compound represented by thefollowing general formula (1):

wherein in the general formula (1), at least one of R¹ to R⁵ representsa cyano group, at least one of R¹ to R⁵ represents a group representedby the following general formula (11), and the balance of R¹ to R⁵represents a hydrogen atom or a substituent;

wherein in the general formula (11), R²¹ to R²⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof the following requirements (A) and (B) is satisfied: (A) R²⁵ and R²⁶jointly form a single bond, and (B) R²⁷ and R²⁸ jointly form an atomicgroup that is required for forming a substituted or unsubstitutedbenzene ring.
 14. The organic light-emitting device according to claim13, which emits delayed fluorescent light.
 15. The organiclight-emitting device according to claim 13, which is an organicelectroluminescent device.
 16. A delayed fluorescent emitter having astructure represented by the following general formula (1):

wherein in the general formula (1), at least one of R¹ to R⁵ representsa cyano group, at least one of R¹ to R⁵ represents a group representedby the following general formula (11), and the balance of R¹ to R⁵represents a hydrogen atom or a substituent;

wherein in the general formula (11), R²¹ to R²⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof the following requirements (A) and (B) is satisfied: (A) R²⁵ and R²⁶jointly form a single bond, and (B) R²⁷ and R²⁸ jointly form an atomicgroup that is required for forming a substituted or unsubstitutedbenzene ring.